Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof

ABSTRACT

A compound represented by Formula 1 is disclosed. An organic electric element includes a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode. The organic material layer includes the compound represented by Formula 1. When the organic electric element includes the compound in the organic material layer, luminescence efficiency, stability, and life span can be improved.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit under 35 U.S.C. §119(a) of Korean Patent Application No. 10-2014-0005580 filed on Jan.16, 2014, and Korean Patent Application No. 10-2014-0086820 filed onJul. 10, 2014, the contents of which are hereby incorporated byreference for all purposes as if fully set forth herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements using the same, and electronicdevices thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy using an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon typically has a structure comprising an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer has a multilayered structure includingmultiple layers made of different materials in order to improve theefficiency and stability of an organic electric element, and forexample, may include a hole injection layer, a hole transport layer, alight emitting layer, an electron transport layer, an electron injectionlayer, or the like.

A material used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Further, the light emitting material may be divided into a highmolecular weight type and a low molecular weight type according to itsmolecular weight, and may also be divided into a fluorescent materialderived from electronic excited singlet states and a phosphorescentmaterial derived from electronic excited triplet states according to itslight emitting mechanism. Further, the light emitting material may bedivided into blue, green, and red light emitting materials, and yellowand orange light emitting materials required for better natural colorreproduction according to its light emitting color.

Meanwhile, when only one material is used as a light emitting material,there occur problems of shift of a maximum luminescence wavelength to alonger wavelength due to intermolecular interactions and lowering of theefficiency of a corresponding element due to deterioration in colorpurity or a reduction in luminescence efficiency. On account of this, ahost/dopant system may be used as the light emitting material in orderto enhance the color purity and increase the luminescence efficiencythrough energy transfer. This is based on the principle that if a smallamount of dopant having a smaller energy band gap than a host forming alight emitting layer is mixed in the light emitting layer, then excitonsgenerated in the light emitting layer are transported to the dopant,thus emitting light with high efficiency. With regard to this, since thewavelength of the host is shifted to the wavelength band of the dopant,light having a desired wavelength can be obtained according the type ofthe dopant.

Currently, the power consumption is required more than more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and life span issue also is solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase. However, efficiency cannot be maximized only bysimply improving the organic material layer. This is because long lifespan and high efficiency can be simultaneously achieved when an optimalcombination of energy levels and T1 values, inherent material properties(mobility, interfacial properties, etc.), and the like among therespective layers included in the organic material layer is given.Therefore it is required to develop a light emitting material that hashigh thermal stability and can achieve efficiently a charge balance inthe light-emitting layer.

Further, in order to solve the emission problem with a hole transportlayer in a recent organic electric element, an emission-auxiliary layeris present between the hole transport layer and a light emitting layer,and it is time to develop different emission-auxiliary layers accordingto respective light emitting layers (R, G, B).

In general, an electron transferred from an electron transport layer toa light emitting layer and a hole transferred from a hole transportlayer to the light emitting layer are recombined to form an exciton.However, since a material used in a hole transporting layer should havea low HOMO value, it mainly has a low T1 value. Due to this, excitonsgenerated from a light emitting layer are transported to the holetransporting layer, resulting in a charge unbalance in the lightemitting layer. Thus, light emission occurs at an interface of the holetransporting layer.

When light emission at an interface of the hole transporting layer, theorganic electroluminescent device also suffers from the disadvantage ofa reduction in color purity, efficiency, and lifespan. Therefore, thereis an urgent need to develop an emission-auxiliary layer which has ahigh T1 value and the HOMO level of which is between the HOMO energylevel of a hole transport layer and the HOMO energy level of a lightemitting layer.

In order to allow an organic electric element to fully exhibit theabove-mentioned excellent features, it should be prerequisite to supporta material constituting an organic material layer in the element, forexample, a hole injection material, a hole transport material, a lightemitting material, an electron transport material, an electron injectionmaterial, or the like, by a stable and efficient material. However, sucha stable and efficient organic material layer material for an organicelectric element has not yet been fully developed. Accordingly, there isa continuous need to develop new materials for an organic materiallayer.

The background art of the present inventions are disclosed in thedocuments below.

PRIOR ART

-   1. U.S. Pat. No. 6,596,415 (2003.7.22)-   2. U.S. Pat. No. 6,465,115 (2002.10.15)-   3. International Publication No. WO2009/148015 (2009.12.10)

SUMMARY

In order to solve one or more of the above-mentioned problems occurringin the prior art, an aspect of the present invention is to provide acompound which allows an organic electric element to have highluminescence efficiency, low driving voltage, high heat-resistant, andto be improved in color purity and life span, an organic electricelement using the same, and an electronic device including the organicelectric element.

In accordance with an aspect of the present invention, the compoundrepresented by the following formula is provided.

In another aspect of the present invention, organic electric elementsusing the compound represented by the formula above and electronicdevices including the organic electric element are provided.

By using the compound according to embodiments of the present invention,an organic electric element according to one or more embodiments of thepresent invention not only has high luminescence efficiency, low drivingvoltage and high heat-resistant, but can also be significantly improvedin color purity, and life span.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

In addition, it will be understood that when an element such as a layer,film, region or substrate is referred to as being “on” or “over” anotherelement, it can be directly on the other element or intervening elementsmay also be present. In contrast, when an element is referred to asbeing “directly on” another element, there are no intervening elementspresent.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means aliphaticfunctional radicals including a linear alkyl group, a branched chainalkyl group, a cycloalkyl group (alicyclic), or an alkyl groupsubstituted with a cycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl” as usedherein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxyl group”, “alkoxy group” or “alkyloxy group” as usedherein means an oxygen radical attached to an alkyl group, but notlimited to, and has 1 to 60 carbon atoms.

The term “aryloxyl group” or “aryloxy group” as used herein means anoxygen radical attached to an aryl group, but not limited to, and has 6to 60 carbon atoms.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means, univalent or bivalent functional groupwhich R, R′ and R″ are all hydrogen in the structural formula below.Also, “substituted fluorenyl group” or “substituted fluorenylene group”means, functional group which at least any one of R, R′ and R″ is afunctional group other than hydrogen and spiro compound which R and R′can be linked together with the carbone to which they are attached toform spiro compound.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. Herein, thearyl group or arylene group means a monocyclic or polycyclic aromaticgroup, and may also be formed in conjunction with an adjacent group.Examples of “aryl group” or “arylene group” may include a phenyl group,a biphenyl group, a fluorene group, or a spirofluorene group.

Unless otherwise stated, the term “heterocyclic group” as used hereinmeans, but not limited to, a non-aromatic ring as well as an aromaticring like “heteroaryl group” or “heteroarylene group”. The heterocyclicgroup as used herein means, but not limited to, a ring containing one ormore heteroatoms, and having 2 to 60 carbon atoms. Unless otherwisestated, the term “heteroatom” as used herein represents at least one ofN, O, S, P, and Si. The heterocyclic group means a monocyclic, ringassemblies, fused polycyclic system or spiro compound containing one ormore heteroatoms.

Also, the term “heterocyclic group” may include SO₂ instead of carbonconsisting of cycle. For example, “heterocyclic group” includes compoundbelow.

Unless otherwise stated, the term “ring” as used herein means, amonocyclic and polycyclic, an aliphatic ring and heterocyclic groupcontaining at least one heteroatom, and an aromatic ring and anon-aromatic ring.

Unless otherwise stated, the term “polycyclic” as used herein means,ring assemblies like biphenyl and terphenyl, fused polycyclic system andspiro compound, an aromatic ring and a non-aromatic ring, and analiphatic ring and heterocyclic group containing at least oneheteroatom.

Unless otherwise stated, the term “ring assemblies” as used hereinmeans, two or more cyclic systems (single rings or fused systems) whichare directly joined to each other by double or single bonds are namedring assemblies when the number of such direct ring junctions is oneless than the number of cyclic systems involved. The ring assembliesalso mean, same or different ring systems are directly joined to eachother by double or single bonds.

Unless otherwise stated, the term “fused polycyclic system” as usedherein means, fused ring type which has at least two atoms as the commonmembers, fused two or more aliphatic ring systems and a fused heteroring system containing at least one heteroatom. Fused polycyclic systemis an aromatic ring, a hetero aromatic ring, an aliphatic ring, or thecombination of these.

Unless otherwise stated, the term “spiro compound” as used herein has, aspiro union which means union having one atom as the only common memberof two rings. The common atom is designated as ‘spiro atom’. Thecompounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’depending on the number of spiro atoms in one compound.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substitutes with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium (D), halogen, an amino group, a nitrile group, a nitro group,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group,a C₁-C₂₀ alkylthio group, a C₆-C₂₀ arylthio group, a C₂-C₂₀ alkenylgroup, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₆₀ arylgroup, a C₆-C₂₀ aryl group substituted by deuterium, a C₆-C₂₀arylalkenyl group, a silane group, a boron group, a germanium group, anda C₂-C₂₀ heterocyclic group.

Otherwise specified, the Formulas used in the present invention are asdefined in the index definition of the substituent of the followingFormula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R¹s may be the same and different, and are linked tothe benzene ring as follows. when a is an integer of 4 to 6, thesubstituents R¹s may be the same and different, and are linked to thebenzene ring in a similar manner to that when a is an integer of 2 or 3,hydrogen atoms linked to carbon constituents of the benzene ring beingnot represented as usual.

The FIGURE illustrates an organic electric element according to anembodiment of the present invention.

Referring to the FIGURE, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer between the first electrode 110 and the second electrode180, which contains the inventive compound. Here, the first electrode120 may be an anode (positive electrode), and the second electrode 180may be a cathode (negative electrode). In the case of an invertedorganic electric element, the first electrode may be a cathode, and thesecond electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, the layers included in the organic materiallayer, except the light emitting layer 150, may not be formed. Theorganic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141, etc., and the electron transport layer 160 and the like may serveas the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer or one capping layer formed on at least one of thesides the first and second electrodes, which is a side opposite to theorganic material layer.

The inventive compound employed in the organic material layer may beused as a host material, a dopant material, or a capping layer materialin the hole injection layer 130, the hole transport layer 140, theelectron transport layer 160, the electron injection layer 170, or thelight emitting layer 150. For example, the inventive compound may beused as the light emitting layer 150, the hole transport layer 140,and/or the emission-auxiliary layer 151.

Since depending on the type and position of a substituent to beattached, a band gap, electrical properties, interfacial properties, andthe like may vary even in the same core, it is very important what thetypes of core and a combination of substituent attached to the core are.Specially, long life span and high efficiency can be simultaneouslyachieved when an optimal combination of energy levels and T1 values,inherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers included in the organicmaterial layer is given.

As already described above, in order to solve the emission problem witha hole transport layer in a conventional organic electric element, anemission-auxiliary layer is preferably formed between the hole transportlayer and a light emitting layer, and it is time to develop differentemission-auxiliary layers according to respective light emitting layers(R, G, B). However, even when a similar core is used, it is verydifficult to infer the characteristics of an emission-auxiliary layer ifa used organic material layer varies because the correlation between theemission-auxiliary layer and a hole transport layer and the correlationbetween the emission-auxiliary layer and a light emitting layer (host)mused be discovered.

Accordingly, in the present invention, a combination of energy levelsand T1 values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers included inthe organic material layer is optimized by forming a light emittinglayer and/or an emission-auxiliary layer by using the compoundrepresented by Formula 1, and thus the life span and efficiency of theorganic electric element can be improved at the same time.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 120, forming the organic material layer including the holeinjection layer 130, the hole transport layer 140, the light emittinglayer 150, the electron transport layer 160, and the electron injectionlayer 170 thereon, and then depositing a material, which can be used asthe cathode 180, thereon. Also, an emitting auxilary layer 151 may becomprised between the hole transport layer 140 and the light emittinglayer 150.

And also, the organic material layer may be manufactured in such amanner that a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, dip coating, doctor blading, screen printing, inkjet printing,or thermal transfer, instead of deposition. Since the organic materiallayer according to the present invention may be formed in various ways,the scope of protection of the present invention is not limited by amethod of forming the organic material layer.

According to used materials, the organic electric element according toan embodiment of the present invention may be of a top emission type, abottom emission type, or a dual emission type.

A WOLED (White Organic Light Emitting Device) readily allows for theformation of ultra-high definition images, and is of excellentprocessability as well as enjoying the advantage of being produced usingconventional color filter technologies for LCDs. In this regard, variousstructures for WOLEDs, used as back light units, have been, in the mostpart, suggested and patented. Representative among the structures are aparallel side-by-side arrangement of R(Red), G (Green), B (Blue)light-emitting units, a vertical stack arrangement of RGB light-emittingunits, and a CCM (color conversion material) structure in whichelectroluminescence from a blue (B) organic light emitting layer, andphotoluminescence from an inorganic luminescent using theelectroluminescence are combined. The present invention is applicable tothese WOLEDs.

Further, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, an organic electric element according to an aspect of thepresent invention will be described.

The compound according to an aspect of the present invention isrepresented by the following Formula 1.

In formula 1 above, each of the symbols may be defined as follows:

Z is S or N(R⁵);

V, W, X and Y are each independently N(R⁶), S or O, provided that atleast one of X, Y, V and W is not N(R⁶) when Z is NR⁵, thereby excludingthe compounds where all of X, Y, V, W, and Z are amine groups; m, n, oand p are each independently an integer of 0 or 1, wherein m+n is 1 ormore and o+p is 1 or more, and wherein m=0, n=0, o=0 or p=0, in eachcase, means that the corresponding bridge X, Y, V or W is not present.

For example, if m+n is 1 or more, at least one of X and Y may be N(R⁶),S or O. Likewise, if o+p may be 1 or more, at least one of V and W maybe N(R⁶), S or O. That is, the compound where m+n is 0 and/or o+p is 0is excluded. Accordingly, the ring including X and Y may be afive-membered ring or a six-membered ring, and the ring including V andW may be a five-membered ring or a six-membered ring.

Specifically, i) when Z is N(R⁵), at least one of V and W is selectedfrom N(R⁶), S or O and at least one of X and Y is selected from N(R⁶), Sor O, with the proviso that the compounds where all of V, W, X and Y areNR⁶ are excluded; and ii) when Z is S, at least one of V and W isselected from N(R⁶), S or O, and at least one of X and Y is selectedfrom N(R⁶), S or O. In either case, however, at least one of X and Y ispresent and at least one of V and W is present.

R⁵ and R⁶ above are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenylene group; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group; -L′-N(Ar¹) (Ar²); and a combination thereof.

Preferably, R⁵ and R⁶ may be each independently, a C₆-C₂₅ aryl group, aC₃-C₁₂ heterocyclic group, a fluorenylene group, or -L′-N(Ar¹) (Ar²),preferably a C₆, C₁₀, or C₁₂ aryl group; a C₃, C₄, C₈, or C₁₂heterocyclic group, particularly, a phenyl, a biphenyl, a naphthyl, afluorenyl unsubstituted or substituted with methyl or phenyl, aspirobifluorenyl, a triazinyl unsubstituted or substituted with phenyl,a pyrimidinyl unsubstituted or substituted with phenyl, a quinazolinylor a dibenzothienyl unsubstituted or substituted with phenyl, naphthyl,biphenyl, terphenyl, phenanthrenyl, triphenyl, fluorenyl, carbazole,dibenzothienyl or dibenzofuryl.

Preferably, R⁵ and R⁶ may be optionally substituted with one or moresubstituent(s) selected from the group consisting of deuterium; halogen;a silan group; a siloxane group; a boron group; a germanium group; acyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group; a C₃-C₂₀cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₉-C₂₀ arylalkenylgroup.

In Formula 1 above, R¹ to R⁴ may be each independently selected from thegroup consisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P; afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group; -L′-N(Ar¹)(Ar²); and acombination thereof.

Each of a and d above may be an integer of 0 to 4, each of b and c maybe an integer of 0 to 2.

When a is 2 or more the plurality of R¹ may be the same or differentfrom each other, when b is 2 the plurality of R² may be the same ordifferent from each other, when c is 2 the plurality of R³ may be thesame or different from each other, and when d is 2 or more the pluralityof R⁴ may be the same or different from each other.

Preferably, R¹ to R⁴ may be each independently, hydrogen, a C₆-C₁₈ arylgroup, a C₃-C₁₂ heterocyclic group, or a diphenyl amine group,preferably a C₆ aryl group, a C₅ or C₁₂ heterocyclic group, particularlyphenyl, pyridyl, carbazole unsubstituted or substituted with phenyl.

Further, any two adjacent groups of R¹ to R⁴ may optionally form a ringthat may be a mono- or poly-cyclic ring, where the other two of R¹ to R⁴not forming a ring may be the same as defined above. Preferably, R¹ toR⁴ may be optionally substituted with one or more substituents selectedfrom the group consisting of deuterium; halogen; a silane group; asiloxane group; a boron group; a germanium group; a cyano group; a nitrogroup; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkylgroup; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ arylgroup; a C₆-C₂₀ aryl group substituted with deuterium; a fluorenylgroup; a C₂-C₂₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P; a C₃-C₂₀cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀ arylalkenylgroup.

L′ may be selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P; and a combination thereof.

Preferably, L′ may be a single bond, a C₆-C₁₈ arylene group, a C₃-C₁₂heterocyclic group, or a fluorenylene group, preferably a C₆ or C₁₂arylene group, a C₄ or C₁₂ heterocyclic group, particularly a phenylenegroup, a biphenylene group, a fluorenylene group unsubstituted orsubstituted with methyl, a pyrimidinyl group, a carbazolylene groupunsubstituted or substituted with a phenyl or dibenzothienyl group.

Preferably, L′ may be optionally substituted with one or moresubstituent(s) selected from the group consisting of deuterium; halogen;a silane group; a siloxane group; a boron group; a germanium group; acyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

Ar¹ and Ar² above may be each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; and a combination thereof.

Preferably, Ar¹ and Ar² may be each independently, a C₆-C₁₈ aryl group,a C₃-C₁₂ heterocyclic group, or a fluorenyl group, preferably a C₆, C₁₀or C₁₂ aryl group, a C₃ or C₁₂ heterocyclic group, particularly phenyl,naphthyl, biphenyl, fluorenyl unsubstituted or substituted with methylor phenyl, triazinyl or dibenzothienyl unsubstituted or substituted withphenyl.

Preferably, Ar¹ and Ar² may be optionally substituted with one or moresubstituents selected from the group consisting of deuterium; halogen; asilane group; a siloxane group; a boron group; a germanium group; acyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxygroup; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.

Particularly, Formula 1 above, in accordance with the combination of m,n, o and p, may be represented by any one of Formulas 2 to 4 below.Formula 2 is an example of Formula 1 wherein m is 1, n is 0, o is 0, andp is 1. Formula 3 is an example of Formula 1 wherein m is 0, n is 1, ois 1, and p is 0. Formula 4 is an example of Formula 1 wherein m is 0, nis 1, o is 0, and p is 1.

In Formula 2 to Formula 4, V, W, X, Y, Z, R¹ to R⁴, a, b, c and d may bethe same as defined in Formula 1 above.

More particularly, the compound represented by Formula 1 above may beany one of the following compounds.

In another aspect of the present invention, a compound for an organicelectric element represented by Formula 1 above is provided.

In another aspect of the present invention, an organic electric elementcomprising the compound represented by Formula 1 above is provided.

The organic electric element can comprise a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode. The organic material layer cancomprise the compound represented by Formula 1. The compound representedFormula 1 can be contained in at least one layer of a hole injectionlayer, a hole transport layer, an emission-auxiliary layer, or a lightemitting layer of the organic material layer. The compound representedby Formula 1 may be used a material in the hole injection layer, amaterial in the hole transport layer, a material in theemission-auxiliary layer, or a material in the light emitting layer.

Specifically, the organic electric element comprising the organicmaterial layer comprising at least one of the compounds represented byFormula 2 to 4 is provided, more specially, the organic electric elementcomprising the organic material layer comprising at least one of thecompounds represented by individual Formula 1-1 to 1-24, 2-1 to 2-40,3-1 to 3-24, 4-1 to 4-40, 5-1 to 5-24, 6-1 to 6-40, 7-1 to 7-24 and 8-1to 8-20 is provided.

Furthermore, the compounds comprising of an organic material layer canbe one kind or two or more different kinds of the compounds representedby Formula 1 above.

As an example, an emission-auxiliary layer or a light emitting layer ofan organic material layer may be formed of a compound 1-1 or comprised amixture of the compound 1-1 and 1-3.

In another aspect of the present invention, the present inventionprovides an organic electric element further including at least a layerto improve luminescence efficiency which is formed on at least one ofthe sides the first and second electrodes, which is opposite to theorganic material layer.

Hereinafter, Synthesis Examples of the inventive compound represented byFormula 1 above and Preparation Examples of an organic electric elementwill be described in detail by way of example. However, the followingexamples are only for illustrative purposes and are not intended tolimit the scope of the invention.

SYNTHESIS EXAMPLE

As an example, the compounds of the present invention can be preparedaccording to, but not limited to, the following reaction scheme 1 orreaction scheme 3 depending on Z of Formula 1.

I. Synthesis Example of the Product 1 (Z═S)

1. Synthesis Example of Sub 1

When X or Y of Sub 1 is NR⁶, it can be synthesized according to, but notlimited to, the following Reaction scheme 2.

A solution of Sub 1-1 (1 eq), Sub 1-2 (1 eq), Pd₂(dba)₃ (0.05 eq), PPh₃(0.1 eq), NaOt-Bu (3 eq), toluene (10.5 mL/Sub1-1 1 mmol) in roundbottom flask was reacted at 100° C. Upon completion of the reaction, thereaction mixture was extracted with diethyl ether and water, then, driedover MgSO₄, concentrated. The concentrate was separated by a silica gelcolumn chromatography and recrystallization to obtain Sub 1-3.

(1) Synthesis Example of Sub 1(1)

Sub 1-1-1 (4.9 g, 20 mmol), Sub 1-2-1 (4.1 g, 20 mmol), Pd₂(dba)₃ (0.9g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60 mmol), and toluene(210 mL) were added in a round bottom flask and reacted at 100° C. Uponcompletion of the reaction, the resulting mixture was extracted withdiethyl ether and water, then, dried over MgSO₄ and concentrated. Theconcentrate was separated by a silica gel column chromatography andrecrystallized to obtain Sub 1(1) (4.8 g, 75%).

(2) Synthesis Example of Sub 1(9)

Sub 1-1-1 (4.9 g, 20 mmol), Sub 1-2-2 (6.6 g, 20 mmol), Pd₂(dba)₃ (0.9g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60 mmol), and toluene(210 mL) were added in a round bottom flask and reacted at 100° C. Uponcompletion of the reaction, the resulting mixture was extracted withdiethyl ether and water, then, dried over MgSO₄, and concentrated. Theconcentrate was separated by a silica gel column chromatography andrecrystallized to obtain Sub 1(9) (6.2 g, 69%).

Examples of Sub 1 compounds include, but are not limited to, thefollowing compounds, and FD-MS data of the compounds are given in Table1 below.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1(1) m/z = 321.02(C₁₈H₁₂BrN =322.20) Sub 1(2) m/z = 371.03(C₂₂H₁₄BrN = 372.26) Sub 1(3) m/z =371.03(C₂₂H₁₄BrN = 372.26) Sub 1(4) m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub1(5) m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub 1(6) m/z = 476.06(C₂₇H₁₇BrN₄ =477.35) Sub 1(7) m/z = 475.07(C₂₈H₁₈BrN₃ = 476.37) Sub 1(8) m/z =475.07(C₂₈H₁₈BrN₃ = 476.37) Sub 1(9) m/z = 449.05(C₂₆H₁₆BrN₃ = 450.33)Sub 1(10) m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub 1(11) m/z = 562.10(C₃₆H₂₃BrN₂ = 563.49) Sub 1(12) m/z = 398.04(C₂₃H₁₅BrN₂ = 399.28) Sub 1(13) m/z= 488.09(C₃₀H₂₁BrN₂ = 489.41) Sub 1(14) m/z = 321.02(C₁₈H₁₂BrN = 322.20)Sub 1(15) m/z = 371.03(C₂₂H₁₄BrN = 372.26) Sub 1(16) m/z =371.03(C₂₂H₁₄BrN = 372.26) Sub 1(17) m/z = 397.05(C₂₄H₁₆BrN = 398.29)Sub 1(18) m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub 1(19) m/z =476.06(C₂₇H₁₇BrN₄ = 477.35) Sub 1(20) m/z = 475.07(C₂₈H₁₈BrN₃ = 476.37)Sub 1(21) m/z = 475.07(C₂₈H₁₈BrN₃ = 476.37) Sub 1(22) m/z =449.05(C₂₆H₁₆BrN₃ = 450.33) Sub 1(23) m/z = 397.05(C₂₄H₁₆BrN = 398.29)Sub 1(24) m/z = 562.10(C₃₆H₂₃BrN₂ = 563.49) Sub 1(25) m/z =261.95(C₁₂H₇BrS = 263.15) Sub 1(26) m/z = 261.95(C₁₂H₇BrS = 263.15) Sub1(27) m/z = 245.97(C₁₂H₇BrO = 247.09) Sub 1(28) m/z = 245.97(C₁₂H₇BrO =247.09)

2. Synthesis Example of Sub 2

A mixture of Sub 1 (1 eq) and tert-butyl lithium (1.1 eq) was stirred at−78° C. for hr. After increasing the reaction temperature to roomtemperature, to the solution was added octathiocane (1.5 eq) and stirredfor 3 hr. And then to the solution was added HCl and stirred for 30 minagain. Upon completion of the reaction, the reaction solution wasextracted with CH₂Cl₂ and water, dried over MgSO₄, concentrated. Theconcentrate was separated by a silica gel column chromatography andrecrystallized to obtain Sub 2.

3. Synthesis Example of Sub 3

Sub 3 was prepared in the same way, but not limited to, as Synthesisexample of Sub 1.

4. Synthesis Example of Sub 4

A mixture of Sub 2 (1 eq.), Sub 3 (1 eq.), potassium tert-butoxide (1.1eq.), (NHC)₂Ni (0.04 eq.) in DMF was stirred for 16 hr at 110° C. Uponcompletion of the reaction, the resulting solution was cooled to roomtemperature, extracted with CH₂Cl₂ and washed with water, dried overanhydrous MgSO₄ to remove a trace amount of water, filtered underpressure and concentrated. The concentrate was separated by a silica gelcolumn chromatography and recrystallized to obtain Sub 4.

5. Synthesis Example of Product 1

A mixture of Sub 4 (1 eq), 12 (1.25 eq) and cyclohexane was added inHanovia photoreactor with 1450 W medium pressure Hg lamp, and stirredunder argon for 20 min. After that, to the resulting mixture was addedpropylene oxide (6 eq) and irradiated for 30 min. Upon completion of thereaction, the reactant was cooled to room temperature, and extractedwith CH₂Cl₂, washed with water, dried over anhydrous MgSO₄ to remove atrace amount of water. Then, the organic layer was filtered underpressure and concentrated. The concentrate was separated by a silica gelcolumn chromatography and recrystallized to obtain Product 1.

(1) Synthesis Example of Product 1-8

1) Synthesis Example of Sub 2(1)

A solution of Sub 1(17) (8.0 g, 20 mmol), tert-butyl lithium (1.4 g, 22mmol) was stirred at −78° C. for 1 hr. After raising the reactiontemperature to room temperature, to the solution was added octathiocane(7.7 g, 30 mmol) and stirred for 3 hr. And HCl was added to the solutionand stirred for 30 min again. Upon completion of the reaction, thereactant was extracted with CH₂Cl₂ and water, dried over MgSO₄ andconcentrated. The concentrate was separated by a silica gel columnchromatography and recrystallization to obtain Sub 2(1) (4.6 g, 65%).

2) Synthesis Example of Sub 4(1)

A solution of Sub 2(1) (7.0 g, 20 mmol), Sub 3(1) (9.0 g, 20 mmol),potassium tert-butoxide (2.5 g, 22 mmol), (NHC)₂Ni (0.67 g, 0.8 mmol) inDMF was stirred at 110° C. for 16 hr. Upon completion of the reaction,the reactant was cooled to room temperature, extracted with CH₂Cl₂,washed with water, dried over MgSO₄ to remove trace amount of water andfiltered under vacuum concentrated. The concentrate was separated by asilica gel column chromatography and recrystallization to obtain Sub4(1) (9.8 g, 68%).

3) Synthesis Example of the Compound 1-8

A solution of Sub 4(1) (14.4 g, 20 mmol), 12 (6.34 g, 25 mmol), andcyclohexane in Hanovia photoreactor with 1450 W medium pressure Hg lampwas stirred under argon for 20 min. Then, propylene oxide (7.0 g, 120mmol) was added to the reaction solution and irradiated for 30 min. Uponcompletion of the reaction, the reactant was cooled to room temperature,extracted with CH₂Cl₂, washed with water, dried over anhydrous MgSO₄ toremove trace amount of water, filtered under pressure and concentrated.The concentrate was separated by a silica gel column chromatography andrecrystallization to obtain Product 1-8 (9.3 g, 65%).

(2) Synthesis Example of the Compound 3-1

1) Synthesis Example of Sub 2(2)

A solution of Sub 1(19) (9.5 g, 20 mmol), tert-butyl lithium (1.4 g, 22mmol) was stirred at −78° C. for 1 hr. After raising the reactiontemperature to room temperature, to the solution was added octathiocane(7.7 g, 30 mmol) and stirred for 3 hr. And HCl was added to the solutionand stirred for 30 min again. Upon completion of the reaction, thereactant was extracted with CH₂Cl₂ and water, dried over MgSO₄ andconcentrated. The concentrate was separated by a silica gel columnchromatography and recrystallization to obtain Sub 2(2) (5.8 g, 67%).

2) Synthesis Example of Sub 4(2)

A solution of Sub 2(2) (8.6 g, 20 mmol), Sub 3(2) (9.0 g, 20 mmol),potassium tert-butoxide (2.5 g, 22 mmol), (NHC)₂Ni (0.67 g, 0.8 mmol) inDMF was stirred at 110° C. for 16 hr. Upon completion of the reaction,the reactant was cooled to room temperature, extracted with CH₂Cl₂,washed with water, dried over MgSO₄ to remove trace amount of water andfiltered under vacuum concentrated. The concentrate was separated by asilica gel column chromatography and recrystallization to obtain Sub4(2) (9.4 g, 70%).

3) Synthesis Example of the Compound 3-1

A solution of Sub 4(2) (13.4 g, 20 mmol), 12 (6.34 g, 25 mmol), andcyclohexane in Hanovia photoreactor with 1450 W medium pressure Hg lampwas stirred under argon for 20 min. Then, propylene oxide (7.0 g, 120mmol) was added to the reaction solution and irradiated for 30 min. Uponcompletion of the reaction, the reactant was cooled to room temperature,extracted with CH₂Cl₂, washed with water, dried over anhydrous MgSO₄ toremove trace amount of water, filtered under pressure and concentrated.The concentrate was separated by a silica gel column chromatography andrecrystallization to obtain Product 3-1 (8.7 g, 65%).

(3) Synthesis Example of the Compound 6-39

1) Synthesis Example of Sub 2(3)

A solution of Sub 1(27) (4.9 g, 20 mmol), tert-butyl lithium (1.4 g, 22mmol) was stirred at −78° C. for 1 hr. Then, after raising the reactiontemperature to room temperature, to the solution was added octathiocane(7.7 g, 30 mmol) and stirred for 3 hr. And HCl was added to the solutionand stirred for 30 min again. Upon completion of the reaction, thereactant was extracted with CH₂Cl₂ and water, dried over MgSO₄ andconcentrated. The concentrate was separated by a silicagel columnchromatography and recrystallization to obtain Sub 2(3) (2.5 g, 62%).

2) Synthesis Example of Sub 4(3)

A solution of Sub 2(3) (4.0, 20 mmol), Sub 3(3) (5.3, 20 mmol),potassium tert-butoxide (2.5 g, 22 mmol), (NHC)₂Ni (0.67 g, 0.8 mmol) inDMF was stirred at 110° C. for 16 hr. Upon completion of the reaction,the reactant was cooled to room temperature, extracted with CH₂Cl₂,washed with water, dried over MgSO₄ to remove trace amount of water andfiltered under vacuum concentrated. The concentrate was separated by asilicagel column chromatography and recrystallization to obtain Sub 4(3)(5.0 g, 66%).

3) Synthesis Example of the Compound 6-39

A solution of Sub 4(3) (7.7 g, 20 mmol), 12 (6.34 g, 25 mmol), andcyclohexane in Hanovia photoreactor with 1450 W medium pressure Hg lampwas stirred under argon for 20 min. Then, propylene oxide (7.0 g, 120mmol) was added to the reaction solution and irradiated for 30 min. Uponcompletion of the reaction, the reactant was cooled to room temperature,extracted with CH₂Cl₂, washed with water, dried over anhydrous MgSO₄ toremove trace amount of water, filtered under pressure and concentrated.The concentrate was separated by a silica gel column chromatography andrecrystallization to obtain Product 6-39 (4.6 g, 61%).

II. Synthesis Example of the Product 2 (Z═NR⁵)

1. Synthesis Example of Sub 5 (1) Synthesis Example of Sub 5-1

1) Synthesis Example of Sub 5-1-3

A solution of Sub 5-1-1 (5.0 g, 20 mmol), Sub 5-1-2 (4.9 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) was added to a round bottom flask. Then, the solution wasrefluxed at 80° C.−90° C. Upon completion of the reaction, it wasdiluted with distilled water at room temperature, extracted withmethylene chloride and water. The organic layer was dried over MgSO₄ andafter concentrating, the concentrate was separated by a silica gelcolumn chromatography and recrystallization to obtain Sub 5-1-3 (3.9 g,60%).

2) Synthesis Example of Sub 5-1-4

A solution of hydrogen peroxide in acetic acid was dropwised to anothersolution of Sub 5-1-3 (6.5 g, 20 mmol) in acetic acid and the reactantwas stirred at room temperature for 6 hr. Upon completion of thereaction, acetic acid was removed by using apparatus for vacuum and thenseparated by a silica gel column chromatography to obtain Sub 5-1-4 (4.6g, 68%).

3) Synthesis Example of Sub 5-1

A mixture of Sub 5-1-4 (6.8 g, 20 mmol) in an excessive amount oftrifluoromethanesulfonic acid was stirred at room temperature for 24 hr,added slowly a solution of water and pyridine (8:1), then refluxed for30 min. After completion of the reaction, the reactant was cooled,extracted with CH₂Cl₂, washed with water and dried over anhydrous MgSO₄to remove trace amount of water and then filtered under pressure andconcentrated. The concentrate was separated by a silica gel columnchromatography and recrystallization to obtain Sub 5-1 (4.1 g, 67%).

(2) Synthesis Example of Sub 5-2

1) Synthesis Example of Sub 5-2-3

Sub 5-2-1 (5.0 g, 20 mmol), Sub 5-2-2 (4.9 g, 20 mmol), Pd(PPh₃)₄ (0.7g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water (30 mL) wereadded to a round bottom flask. Then, the solution was refluxed at 80°C.−90° C. Upon completion of the reaction, it was diluted with distilledwater at room temperature, extracted with methylene chloride and water.The organic layer was dried over MgSO₄ and after concentrating, theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 5-2-3 (4.0 g, 62%).

2) Synthesis Example of Sub 5-2-4

A solution of hydrogen peroxide in acetic acid was dropwised to anothersolution of Sub 5-2-3 (6.5 g, 20 mmol) in acetic acid and then thereactant was stirred at room temperature for 6 hr. Upon completion ofthe reaction, acetic acid was removed by using apparatus for vacuum andthen the concentrate was separated by a silica gel column chromatographyto obtain Sub 5-2-4 (4.8 g, 70%).

3) Synthesis Example of Sub 5-2

A mixture of Sub 5-2-4 (6.8 g, 20 mmol) in an excessive amount oftrifluoromethanesulfonic acid were stirred at room temperature for 24hr, added slowly a solution of water and pyridine (8:1), then refluxedfor 30 min. After completion of the reaction, the reactant was cooled,extracted with CH₂Cl₂, washed with water and dried over anhydrous MgSO₄to remove trace amount of water and then filtered under pressure andconcentrated. The concentrate was separated by a silica gel columnchromatography and recrystallization to obtain Sub 5-2 (4.4 g, 72%).

(3) Synthesis Example of Sub 5-3

1) Synthesis Example of Sub 5-3-3

Sub 5-3-1 (5.0 g, 20 mmol), Sub 5-3-2 (4.9 g, 20 mmol), Pd(PPh₃)₄ (0.7g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water (30 mL) wereadded to a round bottom flask. Then, the solution was refluxed at 80°C.˜90° C. Upon completion of the reaction, it was diluted with distilledwater at room temperature, extracted with methylene chloride and water.The organic layer was dried over MgSO₄ and after concentrating, theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 5-3-3 (4.3 g, 66%).

2) Synthesis Example of Sub 5-3-4

A solution of hydrogen peroxide in acetic acid was dropwised to anothersolution of Sub 5-3-3 (6.5 g, 20 mmol) in acetic acid and the reactantwas stirred at room temperature for 6 hr. Upon completion of thereaction, acetic acid was removed by using apparatus for vacuum and thenseparated by a silica gel column chromatography to obtain Sub 5-3-4 (4.1g, 70%).

3) Synthesis Example of Sub 5-3

Sub 5-3-4 (5.8 g, 20 mmol), Sub 5-3-5 (3.1 g, 20 mmol), pd₂(dba)₃ (0.9g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60 mmol), toluene (210mL) were added to a round bottom flask, and reacted at 100° C. Uponcompletion of the reaction, it was extracted with ether and water, then,the organic layer was dried over MgSO₄ and concentrated. The concentratewas separated by a silica gel column chromatography andrecrystallization to obtain Sub 5-3 (5.4 g, 74%).

(4) Synthesis Example of Sub 5-4

1) Synthesis Example of Sub 5-4-3

A solution of Sub 5-4-1 (5.0 g, 20 mmol), Sub 5-4-2 (4.9 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) in a round bottom flask was refluxed at 80° C.˜90° C. Uponcompletion of the reaction, it was diluted with distilled water at roomtemperature, extracted with methylene chloride and water. The organiclayer was dried over MgSO₄ and after concentrated, the concentratedproduct was separated by a silica gel column chromatography andrecrystallization to obtain Sub 5-4-3 (4.3 g, 67%).

2) Synthesis Example of Sub 5-4-4

A solution of Sub 5-4-3 (6.5 g, 20 mmol) and triphenylphosphine (15.7 g,60 mmol) in o-dichlorobenzene was refluxed for 24 hr. Upon completion ofthe reaction, the solvent was removed by vacuum-distillation. Theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 5-4-4 (4.0 g, 69%).

3) Synthesis Example of Sub 5-4

A solution of Sub 5-4-4 (5.8 g, 20 mmol), Sub 5-4-5 (3.1 g, 20 mmol),pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60mmol), toluene (210 mL) in a round bottom flask were reacted at 100° C.Upon completion of the reaction, the reactant was extracted with etherand water, dried over MgSO₄ and concentrated. The concentrate wasseparated by a silica gel column chromatography and recrystallization toobtain Sub 5-4 (5.5 g, 75%).

2. Synthesis Example of Sub 6 (1) Synthesis Example of Sub 6-1

To a dissolving solution of Sub 6-1-1 (5.4 g, 20 mmol) in anhydrousether was slowly added n-BuLi (2.5M in hexane) (1.4 g, 22 mmol) at −78°C., and stirred for 30 min. After that, Triisopropyl borate (5.6 g, 30mmol) was dropwised to the reactant at −78° C. After stirring at roomtemperature, it was added water and 2N HCl. Upon completion of thereaction, the reactant was extracted with ethyl acetate and water, driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 6-1 (3.3g, 73%).

(2) Synthesis Example of Sub 6-2

1) Synthesis Example of Sub 6-2-3

A solution of Sub 6-2-1 (5.0 g, 20 mmol), Sub 6-2-2 (4.0 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) in round bottom flask was refluxed at 80° C.˜90° C. Uponcompletion of the reaction, it was diluted with distilled water at roomtemperature, extracted with methylene chloride and water. The organiclayer was dried over MgSO₄. After concentrating, the concentrate wasseparated by a silica gel column chromatography and recrystallization toobtain Sub 6-2-3 (3.8 g, 68%).

2) Synthesis Example of Sub 6-2-4

A solution of hydrogen peroxide in acetic acid was dropwised to anothersolution of Sub 6-2-3 (5.6 g, 20 mmol) in acetic acid and stirred atroom temperature for 6 hr. Upon completion of the reaction, acetic acidwas removed by using apparatus for vacuum and then separated by a silicagel column chromatography to obtain Sub 6-2-4 (4.3 g, 72%).

3) Synthesis Example of Sub 6-2-5

A solution of Sub 6-2-4 (5.9 g, 20 mmol) in an excessive amount oftrifluoromethanesulfonic acid was stirred at room temperature for 24 hr,added slowly a solution of water and pyridine (8:1), then refluxed for30 min. After completion of the reaction, the reactant was cooled,extracted with CH₂Cl₂, washed with water and dried over anhydrous MgSO₄to remove trace amount of water and then filtered under pressure andconcentrated. The concentrated product was separated by a silica gelcolumn chromatography and recrystallization to obtain Sub 6-2-5 (3.8 g,73%).

4) Synthesis Example of Sub 6-2

To a dissolving solution of Sub 6-2-5 (5.3 g, 20 mmol) in anhydrousether was slowly added n-BuLi (2.5M in hexane) (1.4 g, 22 mmol) at −78°C., and stirred for 30 min. After that, Triisopropyl borate (5.6 g, 30mmol) was dropwised to the reactant at −78° C. After stirring at roomtemperature, it was added water and 2N HCl. Upon completion of thereaction, the reactant was extracted with ethyl acetate and water, driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 6-2 (3.4g, 75%).

(3) Synthesis Example of Sub 6-3

1) Synthesis Example of Sub 6-3-3

A solution of Sub 6-3-1 (2.4 g, 20 mmol), Sub 6-3-2 (6.6 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) in a round bottom flask was refluxed at 80° C.˜90° C. Uponcompletion of the reaction, it was diluted with distilled water,extracted with methylene chloride and water. The organic layer was driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 6-3-3 (3.1g, 55%).

2) Synthesis Example of Sub 6-3-4

A solution of Sub 6-3-3 (5.6 g, 20 mmol), triphenylphosphine (15.7 g, 60mmol) in o-dichlorobenzene was refluxed for 24 hr. Upon completion ofthe reaction, solvent was removed by vacuum distillation. Theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 6-3-4 (2.8 g, 58%).

3) Synthesis Example of Sub 6-3-6

A solution of Sub 6-3-4 (4.9 g, 20 mmol), Sub 6-3-5 (4.1 g, 20 mmol),pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60mmol), toluene (210 mL) was reacted at 100° C. Upon completion of thereaction, the reactant was extracted with ether and water, dried overMgSO₄ and concentrated. The concentrate was separated by a silica gelcolumn chromatography and recrystallization to obtain Sub 6-3-6 (4.6 g,73%).

4) Synthesis Example of Sub 6-3

To a dissolving solution of Sub 6-3-6 (6.4 g, 20 mmol) in anhydrousether was slowly added n-BuLi (2.5M in hexane) (1.4 g, 22 mmol) at −78°C., and stirred for 30 min. After that, Triisopropyl borate (5.6 g, 30mmol) was dropwised to the reactant at −78° C. After stirring at roomtemperature, it was added water and 2N HCl. Upon completion of thereaction, the reactant was extracted with ethyl acetate and water, driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 6-3 (3.8g, 68%).

(4) Synthesis Example of Sub 6-4

1) Synthesis Example of Sub 6-4-3

A solution of Sub 6-4-1 (2.4 g, 20 mmol), Sub 6-4-2 (6.6 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) in a round bottom flask was refluxed at 80° C.˜90° C. Uponcompletion of the reaction, it was diluted with distilled water,extracted with methylene chloride and water. The organic layer was driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 6-4-3 (3.1g, 56%).

2) Synthesis Example of Sub 6-4-4

A solution of Sub 6-4-3 (5.6 g, 20 mmol), triphenylphosphine (15.7 g, 60mmol) in o-dichlorobenzene was refluxed for 24 hr. Upon completion ofthe reaction, solvent was removed by vacuum distillation. Theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 6-4-4 (3.0 g, 60%).

3) Synthesis Example of Sub 6-4-6

A solution of Sub 6-4-4 (4.9 g, 20 mmol), Sub 6-4-5 (4.1 g, 20 mmol),pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60mmol), toluene (210 mL) was reacted at 100° C. Upon completion of thereaction, the reactant was extracted with ether and water, dried overMgSO₄ and concentrated. The concentrate was separated by a silica gelcolumn chromatography and recrystallization to obtain Sub 6-4-6 (4.8 g,75%).

4) Synthesis Example of Sub 6-4

To a dissolving solution of Sub 6-4-6 (6.4 g, 20 mmol) in anhydrousether was slowly added n-BuLi (2.5M in hexane) (1.4 g, 22 mmol) at −78°C., and stirred for 30 min. After that, Triisopropyl borate (5.6 g, 30mmol) was dropwised to the reactant at −78° C. After stirring at roomtemperature, it was added water and 2N HCl. Upon completion of thereaction, the reactant was extracted with ethyl acetate and water, driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 6-4 (4.1g, 71%).

3. Synthesis Example of Sub 7

A solution of Sub 5 (1 eq), Sub 6 (1 eq), Pd(PPh₃)₄ (0.03 eq), NaOH (3eq), THF, water in a round bottom flask was refluxed at 80° C.˜90° C.Upon completion of the reaction, it was diluted with distilled water,extracted with methylene chloride and water. The organic layer was driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 7.

(1) Synthesis Example of Sub 7-1

A solution of Sub 5-2 (6.2 g, 20 mmol), Sub 6-1 (4.6 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) in a round bottom flask was refluxed at 80° C.˜90° C. Uponcompletion of the reaction, it was diluted with distilled water,extracted with methylene chloride and water. The organic layer was driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 7-1 (5.8g, 71%).

(2) Synthesis Example of Sub 7-2

A solution of Sub 5-1 (6.2 g, 20 mmol), Sub 6-2 (4.6 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) in a round bottom flask was refluxed at 80° C.˜90° C. Uponcompletion of the reaction, it was diluted with distilled water,extracted with methylene chloride and water. The organic layer was driedover MgSO₄ and concentrated. The concentrate was separated by a silicagel column chromatography and recrystallization to obtain Sub 7-2 (5.7g, 69%).

(3) Synthesis Example of Sub 7-3

A solution of Sub 5-2 (6.2 g, 20 mmol), Sub 6-4 (5.7 g, 20 mmol),Pd(PPh₃)₄ (0.7 g, 0.6 mmol), NaOH (2.4 g, 60 mmol), THF (60 mL), water(30 mL) in a round bottom flask was refluxed at 80° C.˜90° C. Uponcompletion of the reaction, upon completion of the reaction, it wasdiluted with distilled water, extracted with methylene chloride andwater. The organic layer was dried over MgSO₄ and concentrated. Theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 7-3 (6.2 g, 66%).

4. Synthesis Example of Sub 8

A solution of Sub 7 (1 eq), triphenylphosphine (3 eq) ino-dichlorobenzene was refluxed for 24 hr. Upon completion of thereaction, solvent was removed by vacuum distillation. The concentratewas separated by a silica gel column chromatography andrecrystallization to obtain Sub 8.

(1) Synthesis Example of Sub 8-1

A solution of Sub 7-1 (8.2 g, 20 mmol), triphenylphosphine (15.7 g, 60mmol) in o-dichlorobenzene was refluxed for 24 hr. Upon completion ofthe reaction, solvent was removed by vacuum distillation. Theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 8-1 (5.2 g, 68%)

(2) Synthesis Example of Sub 8-2

A solution of Sub 7-2 (8.2 g, 20 mmol), triphenylphosphine (15.7 g, 60mmol) in o-dichlorobenzene was refluxed for 24 hr. Upon completion ofthe reaction, solvent was removed by vacuum distillation. Theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub 8-2 (5.1 g, 67%)

(3) Synthesis Example of Sub 8-3

A solution of Sub 7-3 (9.4 g, 20 mmol), triphenylphosphine (15.7 g, 60mmol) in o-dichlorobenzene was refluxed for 24 hr. Upon completion ofthe reaction, solvent was removed by vacuum distillation. Theconcentrate was separated by a silica gel column chromatography andrecrystallization to obtain Sub8B-3 (5.1 g, 65%).

5. Example of Sub 9

Examples of Sub 9 compounds include, but are not limited to, thefollowing compounds, and FD-MS data of the compounds are given in Table2 below.

TABLE 2 Compound FD-MS Compound FD-MS Sub 9-1 m/z = 155.96(C₆H₅Br =157.01) Sub9-2 m/z = 205.97(C₁₀H₇Br = 207.07) Sub 9-3 m/z =205.97(C₁₀H₇Br = 207.07) Sub9-4 m/z = 231.99(C₁₂H₉Br = 233.10) Sub 9-5m/z = 309.02(C₁₇H₁₂BrN = 310.19) Sub9-6 m/z = 311.01(C₁₅H₁₀BrN₃ =312.16) Sub 9-7 m/z = 310.01(C₁₆H₁₁BrN₂ = 311.18) Sub9-8 m/z =310.01(C₁₆H₁₁BrN₂ = 311.18) Sub9-9 m/z = 310.01(C₁₆H₁₁BrN₂ = 311.18)Sub9-10 m/z = 387.04(C₂₁H₁₄BrN₃ = 388.26) Sub9-11 m/z =386.04(C₂₂H₁₅BrN₂ = 387.27) Sub9-12 m/z = 386.04(C₂₂H₁₅BrN₂ = 387.27)Sub9-13 m/z = 348.03(C₁₉H₁₃BrN₂ = 349.22) Sub9-14 m/z = 271.99(C₁₃H₉BrN₂= 273.13) Sub 9-15 m/z = 283.99(C₁₄H₉BrN₂ = 285.14) Sub 9-16 m/z =374.01(C₂₀H₁₁BrN₂O = 375.22) Sub 9-17 m/z = 400.06(C₂₃H₁₇BrN₂ = 401.30)Sub 9-18 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.23) Sub 9-19 m/z =476.09(C₂₉H₂₁BrN₂ = 477.39) Sub 9-20 m/z = 284.99(C₁₃H₈BrN₃ = 286.13)Sub 9-21 m/z = 284.99(C₁₃H₈BrN₃ = 286.13) Sub 9-22 m/z =284.99(C₁₃H₈BrN₃ = 286.13) Sub 9-23 m/z = 375.00(C₁₉H₁₀BrN₃O = 376.2)Sub 9-24 m/z = 401.05(C₂₂H₁₆BrN₃ = 402.29) Sub 9-25 m/z =323.03(C₁₈H₁₄BrN = 324.21) Sub 9-26 m/z = 373.05(C₂₂H₁₆BrN = 374.27) Sub9-27 m/z = 373.05(C₂₂H₁₆BrN = 374.27) Sub 9-28 m/z = 475.09(C₃₀H₂₂BrN =476.41) Sub 9-29 m/z = 413.04(C₂₄H₁₆BrNO = 414.3) Sub 9-30 m/z =429.02(C₂₄H₁₆BrNS = 430.36) Sub 9-31 m/z = 439.09(C₂₇H₂₂BrN = 440.37)Sub 9-32 m/z = 563.12(C₃₇H₂₆BrN = 564.51) Sub 9-33 m/z =561.11(C₃₇H₂₄BrN = 562.50) Sub 9-34 m/z = 423.06(C₂₆H₁₈BrN = 424.33)

6. Synthesis Example of Product 2

A solution of Sub 8 (1 eq), Sub 9 (1 eq), Pd₂(dba)₃ (0.05 eq), PPh₃ (0.1eq), NaOt-Bu (3 eq), toluene (10.5 mL/Sub 8 1 mmol) in a round bottomflask was reacted at 100° C. Upon completion of the reaction, it wasextracted with ether and water, dried over MgSO₄. After concentrating,the residue was purified by silica gel column and recrystallization toobtain final product 2.

(1) Synthesis Example of Product 2-5

A solution of Sub 8-1 (7.6 g, 20 mmol), Sub 9-6 (7.5 g, 20 mmol),Pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60mmol), toluene (210 mL) in a round bottom flask was refluxed at 100° C.for 24 hr. Upon completion of the reaction, it was extracted with etherand water, dried over MgSO₄. After concentrating, the residue waspurified by silica gel column and recrystallization to obtain finalproduct 2-5 (8.8 g, 72%).

(2) Synthesis Example of Product 4-16

A solution of Sub 8-2 (7.6 g, 20 mmol), Sub 9-28 (11.4 g, 20 mmol),Pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60mmol), toluene (210 mL) in a round bottom flask was refluxed at 100° C.for 24 hr. Upon completion of the reaction, it was extracted with etherand water, dried over MgSO₄. After concentrating, the residue waspurified by silica gel column and recrystallization to obtain finalproduct 4-16 (10.8 g, 70%).

(3) Synthesis Example of Product 6-33

A solution of Sub 8-3 (8.8 g, 20 mmol), Sub 9-15 (6.8 g, 20 mmol),Pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 2 mmol), NaOt-Bu (5.8 g, 60mmol), toluene (210 mL) in a round bottom flask was refluxed at 100° C.for 24 hr. Upon completion of the reaction, it was extracted with etherand water, dried over MgSO₄. After concentrating, the residue waspurified by silica gel column and recrystallization to obtain finalproduct 6-33 (8.9 g, 69%).

TABLE 3 Compound FD-MS Compound FD-MS 1-1 m/z = 669.20(C₄₅H₂₇N₅S =669.79) 1-2 m/z = 668.20(C₄₆H₂₈N₄S = 668.81) 1-3 m/z = 668.20(C₄₆H₂₈N₄S= 668.81) 1-4 m/z = 642.19(C₄₄H₂₆N₄S = 642.77) 1-5 m/z =745.23(C₅₁H₃₁N₅S = 745.89) 1-6 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 1-7 m/z= 744.23(C₅₂H₃₂N₄S = 744.90) 1-8 m/z = 718.22(C₅₀H₃₀N₄S = 718.87) 1-9m/z = 745.23(C₅₁H₃₁N₅S = 745.89) 1-10 m/z = 744.23(C₅₂H₃₂N₄S = 744.90)1-11 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 1-12 m/z = 718.22(C₅₀H₃₀N₄S =718.87) 1-13 m/z = 719.21(C₄₉H₂₉N₅S = 719.85) 1-14 m/z =178.22(C₅₀H₃₀N₄S = 718.87) 1-15 m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 1-16m/z = 692.20(C₄₈H₂₈N₄S = 692.83) 1-17 m/z = 719.21(C₄₉H₂₉N₅S = 719.85)1-18 m/z =178.22(C₅₀H₃₀N₄S =718.87) 1-19 m/z = 178.22(C₅₀H₃₀N₄S =718.87) 1-20 m/z = 692.20(C₄₈H₂₈N₄S = 692.83) 1-21 m/z =590.18(C₄₂H₂₆N₂S = 590.73) 1-22 m/z = 755.24(C₅₄H₃₃N₃S = 755.92) 1-23m/z = 591.18(C₄₁ H₂₅N₃S = 591.72) 1-24 m/z = 681.22(C₄₈H₃₁N₃S = 681.84)2-1 m/z = 455.08(C₃₀H₁₇NS₂ = 455.59) 2-2 m/z = 777.31 (C₅₈H₃₉N₃ =777.95) 2-3 m/z = 455.08(C₃₀H₁₇NS₂ = 455.59) 2-4 m/z = 531.11(C₃₆H₂₁NS₂= 531.69) 2-5 m/z = 610.13(C₃₉H₂₂N₄S₂ = 610.75) 2-6 m/z =609.13(C₄₀H₂₃N₃S₂ = 609.76) 2-7 m/z = 609.13(C₄₀H₂₃N₃S₂ = 609.76) 2-8m/z = 583.12(C₃₈H₂₁N₃S₂ = 583.72) 2-9 m/z = 561.07(C₃₆H₁₉NS₃ = 561.74)2-10 m/z = 571.14(C₃₉H₂₅NS₂ = 571.75) 2-11 m/z = 695.17(C₄₉H₂₉NS₂ =695.89) 2-12 m/z = 693.16(C₄₉H₂₇NS₂ = 693.88) 2-13 m/z =622.15(C₄₂H₂₆N₂S₂ = 622.80) 2-14 m/z = 672.17(C₄₆H₂₈N₂S₂ = 672.86) 2-15m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 2-16 m/z = 774.22(C₅₄H₃₄N₂S₂ = 774.99)2-17 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 2-18 m/z = 748.20(C₅₂H₃₂N₂S₂ =748.95) 2-19 m/z = 748.20(C₅₂H₃₂N₂S₂ = 748.95) 2-20 m/z =774.22(C₅₄H₃₄N₂S₂ = 774.99) 2-21 m/z = 853.23(C₅₇H₃₅N₅S₂ = 854.05) 2-22m/z = 774.22(C₅₄H₃₄N₂S₂ = 774.99) 2-23 m/z = 824.23(C₅₈H₃₆N₂S₂ = 825.05)2-24 m/z = 824.23(C₅₈H₃₆N₂S₂ = 825.05) 2-25 m/z = 850.25(C₆₀H₃₈N₂S₂ =851.09) 2-26 m/z = 890.28(C₆₃H₄₂N₂S₂ = 891.15) 2-27 m/z =880.20(C₆₀H₃₆N₂S₃ = 881.14) 2-28 m/z = 1014.31(C₇₃H₄₆N₂S₂ = 1015.29)2-29 m/z = 890.28(C₆₃ H₄₂N₂S₂ = 891.15) 2-30 m/z = 776.21(C₅₂H₃₂N₄S₂ =776.97) 2-31 m/z = 880.20(C₆₀H₃₆N₂S₃ = 881.14) 2-32 m/z =939.27(C₆₆H₄₁N₃S₂ = 940.18) 2-33 m/z = 642.19(C₄₄H₂₆N₄S = 642.77) 2-34m/z = 626.21(C₄₄H₂₆N₄O = 626.70) 2-35 m/z = 567.14(C₃₈H₂₁N₃OS = 567.66)2-36 m/z = 551.16(C₃₈H₂₁N₃O₂ = 551.59) 2-37 m/z = 567.14(C₃₈H₂₁N₃OS =567.66) 2-38 m/z = 583.12(C₃₈H₂₁N₃S₂ = 583.72) 2-39 m/z =380.03(C₂₄H₁₂OS₂ = 380.48) 2-40 m/z = 364.06(C₂₄H₁₂O₂S = 364.42) 3-1 m/z= 669.20(C₄₅H₂₇N₅S = 669.79) 3-2 m/z = 668.20(C₄₆H₂₈N₄S = 668.81) 3-3m/z = 668.20(C₄₆H₂₈N₄S = 668.81) 3-4 m/z = 642.19(C₄₄H₂₆N₄S = 642.77)3-5 m/z = 745.23(C₅₁H₃₁N₅S = 745.89) 3-6 m/z = 744.23(C₅₂H₃₂N₄S =744.90) 3-7 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 3-8 m/z = 718.22(C₅₀H₃₀N₄S= 718.87) 3-9 m/z = 745.23(C₅₁H₃₁N₅S = 745.89) 3-10 m/z =744.23(C₅₂H₃₂N₄S = 744.90) 3-11 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 3-12m/z = 718.22(C₅₀H₃₀N₄S = 718.87) 3-13 m/z = 719.21(C₄₉H₂₉N₅S = 719.85)3-14 m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 3-15 m/z = 178.22(C₅₀H₃₀N₄S =718.87) 3-16 m/z = 692.20(C₄₈H₂₈N₄S = 692.83) 3-17 m/z =719.21(C₄₉H₂₉N₅S = 719.85) 3-18 m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 3-19m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 3-20 m/z = 692.20(C₄₈H₂₈N₄S = 692.83)3-21 m/z = 590.18(C₄₂H₂₆N₂S = 590.73) 3-22 m/z = 755.24(C₅₄H₃₃N₃S =755.92) 3-23 m/z = 591.18(C₄₁ H₂₅N₃S = 591.72) 3-24 m/z =681.22(C₄₈H₃₁N₃S = 681.84) 4-1 m/z = 455.08(C₃₀H₁₇NS₂ = 455.59) 4-2 m/z= 777.31(C₅₈H₃₉N₃ = 777.95) 4-3 m/z = 455.08(C₃₀H₁₇NS₂ = 455.59) 4-4 m/z= 531.11(C₃₆H₂₁NS₂ = 531.69) 4-5 m/z = 610.13(C₃₉H₂₂N₄S₂ = 610.75) 4-6m/z = 609.13(C₄₀H₂₃N₃S₂ = 609.76) 4-7 m/z = 609.13(C₄₀H₂₃N₃S₂ = 609.76)4-8 m/z = 583.12(C₃₈H₂₁N₃S₂ = 583.72) 4-9 m/z = 561.07(C₃₆H₁₉NS₃ =561.74) 4-10 m/z = 571.14(C₃₉H₂₅NS₂ = 571.75) 4-11 m/z =695.17(C₄₉H₂₉NS₂ = 695.89) 4-12 m/z = 69 3.16(C₄₉H₂₇NS₂ = 693.88) 4-13m/z = 622.15(C₄₂H₂₆N₂S₂ = 622.80) 4-14 m/z = 672.17(C₄₆H₂₈N₂S₂ = 672.86)4-15 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 4-16 m/z = 774.22(C₅₄H₃₄N₂S₂ =774.99) 4-17 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 4-18 m/z =748.20(C₅₂H₃₂N₂S₂ = 748.95) 4-19 m/z = 748.20(C₅₂H₃₂N₂S₂ = 748.95) 4-20m/z = 774.22(C₅₄H₃₄N₂S₂ = 774.99) 4-21 m/z = 853.23(C₅₇H₃₅N₅S₂ = 854.05)4-22 m/z = 774.22(C₅₄H₃₄N₂S₂ = 774.99) 4-23 m/z = 824.23(C₅₈H₃₆N₂S₂ =825.05) 4-24 m/z = 824.23(C₅₈H₃₆N₂S₂ = 825.05) 4-25 m/z =850.25(C₆₀H₃₈N₂S₂ = 851.09) 4-26 m/z = 890.28(C₆₃H₄₂N₂S₂ = 891.15) 4-27m/z = 880.20(C₆₀H₃₆N₂S₃ = 881.14) 4-28 m/z = 1014.31(C₇₃H₄₆N₂S₂ =1015.29) 4-29 m/z = 890.28(C₆₃ H₄₂N₂S₂ = 891.15) 4-30 m/z =776.21(C₅₂H₃₂N₄S₂ = 776.97) 4-31 m/z = 880.20(C₆₀H₃₆N₂S₃ = 881.14) 4-32m/z = 939.27(C₆₆H₄₁N₃S₂ = 940.18) 4-33 m/z = 642.19(C₄₄H₂₆N₄S = 642.77)4-34 m/z = 626.21(C₄₄H₂₆N₄O = 626.70) 4-35 m/z = 567.14(C₃₈H₂₁N₃OS =567.66) 4-36 m/z = 551.16(C₃₈H₂₁N₃O₂ = 551.59) 4-37 m/z =567.14(C₃₈H₂₁N₃OS = 567.66) 4-38 m/z = 583.12(C₃₈H₂₁N₃S₂ = 583.72) 4-39m/z = 380.03(C₂₄H₁₂OS₂ = 380.48) 4-40 m/z = 364.06(C₂₄H₁₂O₂S = 364.42)5-1 m/z = 669.20(C₄₅H₂₇N₅S = 669.79) 5-2 m/z = 668.20(C₄₆H₂₈N₄S =668.81) 5-3 m/z = 668.20(C₄₆H₂₈N₄S = 668.81) 5-4 m/z = 642.19(C₄₄H₂₆N₄S= 642.77) 5-5 m/z = 745.23(C₅₁H₃₁N₅S = 745.89) 5-6 m/z =744.23(C₅₂H₃₂N₄S = 744.90) 5-7 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 5-8 m/z= 718.22(C₅₀H₃₀N₄S = 718.87) 5-9 m/z = 745.23(C₅₁H₃₁N₅S = 745.89) 5-10m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 5-11 m/z = 744.23(C₅₂H₃₂N₄S = 744.90)5-12 m/z = 718.22(C₅₀H₃₀N₄S = 718.87) 5-13 m/z = 719.21(C₄₉H₂₉N₅S=719.85) 5-14 m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 5-15 m/z =178.22(C₅₀H₃₀N₄S = 718.87) 5-16 m/z = 692.20(C₄₈H₂₈N₄S = 692.83) 5-17m/z = 719.21(C₄₉H₂₉N₅S = 719.85) 5-18 m/z = 178.22(C₅₀H₃₀N₄S = 718.87)5-19 m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 5-20 m/z = 692.20(C₄₈H₂₈N₄S =692.83) 5-21 m/z = 590.18(C₄₂H₂₆N₂S = 590.73) 5-22 m/z =755.24(C₅₄H₃₃N₃S = 755.92) 5-23 m/z = 591.18(C₄₁H₂₅N₃S = 591.72) 5-24m/z = 681.22(C₄₈H₃₁N₃S = 681.84) 6-1 m/z = 455.08(C₃₀H₁₇NS₂= 455.59) 6-2m/z = 777.31(C₅₈H₃₉N₃ = 777.95) 6-3 m/z = 455.08(C₃₀H₁₇NS₂ = 455.59) 6-4m/z = 531.11(C₃₆H₂₁NS₂ = 531.69) 6-5 m/z = 610.13(C₃₉H₂₂N₄S₂ = 610.75)6-6 m/z = 609.13(C₄₀H₂₃N₃S₂ = 609.76) 6-7 m/z = 609.13(C₄₀H₂₃N₃S₂ =609.76) 6-8 m/z = 583.12(C₃₈H₂₁ N₃S₂ = 583.72) 6-9 m/z =561.07(C₃₆H₁₉NS₃ = 561.74) 6-10 m/z = 571.14(C₃₉H₂₅NS₂ = 571.75) 6-11m/z = 695.17(C₄₉H₂₉NS₂ = 695.89) 6-12 m/z = 693.16(C₄₉H₂₇NS₂ = 693.88)6-13 m/z = 622.15(C₄₂H₂₆N₂S₂ = 622.80) 6-14 m/z = 672.17(C₄₆H₂₈N₂S₂ =672.86) 6-15 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 6-16 m/z =774.22(C₅₄H₃₄N₂S₂ = 774.99) 6-17 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 6-18m/z = 748.20(C₅₂H₃₂N₂S₂ = 748.95) 6-19 m/z = 748.20(C₅₂H₃₂N₂S₂ = 748.95)6-20 m/z = 774.22(C₅₄H₃₄N₂S₂ = 774.99) 6-21 m/z = 853.23(C₅₇H₃₅N₅S₂ =854.05) 6-22 m/z = 774.22(C₅₄H₃₄N₂S₂ = 774.99) 6-23 m/z =824.23(C₅₈H₃₆N₂S₂ = 825.05) 6-24 m/z = 824.23(C₅₈H₃₆N₂S₂ = 825.05) 6-25m/z = 850.25(C₆₀H₃₈N₂S₂ = 851.09) 6-26 m/z = 890.28(C₆₃H₄₂N₂S₂ = 891.15)6-27 m/z = 880.20(C₆₀H₃₆N₂S₃ = 881.14) 6-28 m/z = 1014.31(C₇₃H₄₆N₂S₂ =1015.29) 6-29 m/z = 890.28(C₆₃H₄₂N₂S₂ = 891.15) 6-30 m/z =776.21(C₅₂H₃₂N₄S₂ = 776.97) 6-31 m/z = 880.20(C₆₀H₃₆N₂S₃ = 881.14) 6-32m/z = 939.27(C₆₆H₄₁N₃S₂ = 940.18) 6-33 m/z = 642.19(C₄₄H₂₆N₄S = 642.77)6-34 m/z = 626.21(C₄₄H₂₆N₄O = 626.70) 6-35 m/z = 567.14(C₃₈H₂₁N₃OS =567.66) 6-36 m/z = 551.16(C₃₈H₂₁N₃O₂ = 551.59) 6-37 m/z =567.14(C₃₈H₂₁N₃OS = 567.66) 6-38 m/z = 583.12(C₃₈H₂₁N₃S₂ = 583.72) 6-39m/z = 380.03(C₂₄H₁₂OS₂ = 380.48) 6-40 m/z = 364.06(C₂₄H₁₂O₂S = 364.42)7-1 m/z = 669.20(C₄₅H₂₇N₅S = 669.79) 7-2 m/z = 668.20(C₄₆H₂₈N₄S =668.81) 7-3 m/z = 668.20(C₄₆H₂₈N₄S = 668.81) 7-4 m/z = 642.19(C₄₄H₂₆N₄S= 642.77) 7-5 m/z = 745.23(C₅₁H₃₁N₅S = 745.89) 7-6 m/z =744.23(C₅2H₃₂N₄S =744.90) 7-7 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 7-8 m/z =718.22(C₅₀H₃₀N₄S = 718.87) 7-9 m/z = 745.23(C₅₁H₃₁N₅S = 745.89) 7-10 m/z= 744.23(C₅₂H₃₂N₄S = 744.90) 7-11 m/z = 744.23(C₅₂H₃₂N₄S = 744.90) 7-12m/z = 718.22(C₅₀H₃₀N₄S = 718.87) 7-13 m/z = 719.21(C₄₉H₂₉N₅S = 719.85)7-14 m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 7-15 m/z = 178.22(C₅₀H₃₀N₄S =718.87) 7-16 m/z = 692.20(C₄₈H₂₈N₄S = 692.83) 7-17 m/z =719.21(C₄₉H₂₉N₅S = 719.85) 7-18 m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 7-19m/z = 178.22(C₅₀H₃₀N₄S = 718.87) 7-20 m/z = 692.20(C₄₈H₂₈N₄S = 692.83)7-21 m/z = 590.18(C₄₂H₂₆N₂S = 590.73) 7-22 m/z = 755.24(C₅₄H₃₃N₃S =755.92) 7-23 m/z = 591.18(C₄₁H₂₅N₃5 = 591.72) 7-24 m/z =681.22(C₄₈H₃₁N₃S = 681.84) 8-1 m/z = 455.08(C₃₀H₁₇NS₂ = 455.59) 8-2 m/z= 777.31(C₅₈H₃₉N₃ = 777.95) 8-3 m/z = 455.08(C₃₀H₁₇NS₂ = 455.59) 8-4 m/z= 531.11(C₃₆H₂₁NS₂ = 531.69) 8-5 m/z = 610.13(C₃₉H₂₂N₄S₂ = 610.75) 8-6m/z = 609.13(C₄₀H₂₃N₃S₂ = 609.76) 8-7 m/z = 609.13(C₄₀H₂₃N₃S₂ = 609.76)8-8 m/z = 583.12(C₃₈H₂₁N₃S₂ = 583.72) 8-9 m/z = 561.07(C₃₆H₁₉NS₃ =561.74) 8-10 m/z = 571.14(C₃₉H₂₅NS₂ = 571.75) 8-11 m/z =695.17(C₄₉H₂₉NS₂ = 695.89) 8-12 m/z = 693.16(C₄₉H₂₇NS₂ = 693.88) 8-13m/z = 622.15(C₄₂H₂₆N₂S₂ = 622.80) 8-14 m/z = 672.17(C₄₆H₂₈N₂S₂ = 672.86)8-15 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 8-16 m/z = 774.22(C₅₄H₃₄N₂S₂ =774.99) 8-17 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 8-18 m/z =748.20(C₅₂H₃₂N₂S₂ = 748.95) 8-19 m/z = 748.20(C₅₂H₃₂N₂S₂ = 748.95) 8-20m/z = 774.22(C₅₄H₃₄N₂S₂ = 774.99)

Fabrication and Evaluation of Organic Electronic Element

[Example 1] Red Organic Light Emitting Diode (a Phosphorescent Host)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as aphosphorescent host material.

First, an ITO layer (anode) was formed on a glass substrate, and a filmofN¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter abbreviated as “2-TNATA”) was vacuum-deposited on the ITOlayer to form a hole injection layer with a thickness of 60 nm.Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafterabbreviated as “NPD”) was vacuum-deposited with a thickness of 60 nm onthe hole injection layer to form a hole transport layer. Subsequently, alight emitting layer with a thickness of 30 nm was deposited on the holetransport layer by doping the hole transport layer with the compound 1-4of the present invention as a host material andbis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafterabbreviated as “(piq)₂Ir(acac)” as a dopant material in a weight ratioof 95:5.

Next, a film of((1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as “BAlq”) was vacuum-deposited with athickness of 10 nm on the light emitting layer to form a hole blockinglayer, and a film of tris(8-quinolinolato)aluminum (hereinafterabbreviated as “Alq₃”) was formed with a thickness of 40 nm to form anelectron transport layer. Next, LiF as halogenated alkali metal wasdeposited with a thickness of 0.2 nm on the electron transport layer toform an electron injection layer, and then Al was deposited with athickness of 150 nm on the electron injection layer to form a cathode.In this way, the OLED was completed.

[Example 2] to [Example 36] Red Organic Light Emitting Diode (aPhosphorescent Host)

The OLEDs were manufactured in the same manner as described in Example1, except that any one of the compounds 1-8, 1-12, 1-16, 1-20, 2-8, 2-33to 2-38, 3-4, 3-8, 3-12, 3-16, 3-20, 4-8, 4-33 to 4-38, 5-4, 5-8, 5-12,5-16, 5-20, 6-8, 6-33 to 6-38 of the present invention in the Table 4below was used as the host material of the light emitting layer, insteadof the inventive compound 1-4.

Comparative Example 1

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound A was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-4.

Comparative Example 2

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound B was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-4.

Comparative Example 3

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound C was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-4.

Comparative Example 4

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound D was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-4.

Comparative Example 5

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound E was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-4.

Comparative Example 6

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound F was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-4.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough the Examples 1 to 36 and the Comparative Examples 1 to 6, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T90 life span was measured by life spanmeasuring equipment (Mcscience) at the reference brightness of 2500cd/m². Evaluation results are in the Table 4 below.

TABLE 4 Voltage Current Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) (x, y) Com. Ex (1) Com. Com A6.8 34.2 2500.0 7.3 51.6 (0.66, 0.32) Com. Ex (2) Com. Com B 6.9 31.32500.0 8.0 76.6 (0.67, 0.32) Com. Ex (3) Com. Com C 6.7 30.1 2500.0 8.374.3 (0.66, 0.32) Com. Ex (4) Com. Com D 6.5 28.7 2500.0 8.7 71.3 (0.66,0.33) Com. Ex (5) Com. Com E 6.3 26.9 2500.0 9.3 72.5 (0.65, 0.32) Com.Ex (6) Com. Com F 6.1 25.6 2500.0 9.8 85.8 (0.66, 0.32) Ex. (1) 1-4 5.823.3 2500.0 10.7 117.7 (0.66, 0.33) Ex. (2) 1-8 5.6 16.9 2500.0 14.8103.6 (0.66, 0.32) Ex. (3) 1-12 5.3 20.0 2500.0 12.5 95.6 (0.65, 0.32)Ex. (4) 1-16 5.7 16.7 2500.0 15.0 128.2 (0.66, 0.32) Ex. (5) 1-20 5.423.5 2500.0 10.6 105.9 (0.66, 0.32) Ex. (6) 2-8 5.3 21.7 2500.0 11.5109.8 (0.67, 0.32) Ex. (7) 2-33 5.5 18.3 2500.0 13.7 99.9 (0.66, 0.32)Ex. (8) 2-34 5.6 18.4 2500.0 13.6 98.0 (0.66, 0.32) Ex. (9) 2-35 5.419.4 2500.0 12.9 98.6 (0.66, 0.33) Ex. (10) 2-36 5.4 19.5 2500.0 12.8129.7 (0.66, 0.32) Ex. (11) 2-37 5.3 17.3 2500.0 14.5 136.3 (0.65, 0.32)Ex. (12) 2-38 5.6 19.9 2500.0 12.5 123.3 (0.66, 0.32) Ex. (13) 3-4 5.823.6 2500.0 10.6 90.7 (0.66, 0.32) Ex. (14) 3-8 5.3 18.0 2500.0 13.9126.9 (0.67, 0.32) Ex. (15) 3-12 5.6 22.7 2500.0 11.0 137.8 (0.66, 0.32)Ex. (16) 3-16 5.6 24.6 2500.0 10.2 126.8 (0.67, 0.32) Ex. (17) 3-20 5.822.2 2500.0 11.2 145.7 (0.66, 0.32) Ex. (18) 4-8 5.7 18.9 2500.0 13.2108.5 (0.66, 0.32) Ex. (19) 4-33 5.7 18.2 2500.0 13.8 97.7 (0.66, 0.33)Ex. (20) 4-34 5.7 19.6 2500.0 12.8 118.5 (0.66, 0.32) Ex. (21) 4-35 5.523.7 2500.0 10.5 132.4 (0.65, 0.32) Ex. (22) 4-36 5.7 17.4 2500.0 14.3114.4 (0.66, 0.32) Ex. (23) 4-37 5.5 18.9 2500.0 13.2 131.1 (0.66, 0.32)Ex. (24) 4-38 5.4 20.6 2500.0 12.2 118.8 (0.67, 0.32) Ex. (25) 5-4 5.719.1 2500.0 13.1 96.2 (0.66, 0.32) Ex. (26) 5-8 5.6 21.6 2500.0 11.6138.3 (0.67, 0.32) Ex. (27) 5-12 5.7 20.5 2500.0 12.2 141.1 (0.66, 0.32)Ex. (28) 5-16 5.6 19.5 2500.0 12.8 119.0 (0.66, 0.32) Ex. (29) 5-20 5.517.3 2500.0 14.5 145.5 (0.66, 0.33) Ex. (30) 6-8 5.7 21.2 2500.0 11.8105.1 (0.66, 0.32) Ex. (31) 6-33 5.5 20.8 2500.0 12.0 145.9 (0.65, 0.32)Ex. (32) 6-34 5.6 20.1 2500.0 12.5 133.8 (0.66, 0.32) Ex. (33) 6-35 5.424.3 2500.0 10.3 99.0 (0.66, 0.32) Ex. (34) 6-36 5.6 17.0 2500.0 14.7105.7 (0.67, 0.32) Ex. (35) 6-37 5.4 17.0 2500.0 14.7 145.8 (0.66, 0.32)Ex. (36) 6-38 5.4 19.9 2500.0 12.5 105.8 (0.67, 0.32)

[Example 37] Green Organic Light Emitting Diode (a Phosphorescent Host)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as aphosphorescent host material. First, an ITO layer (anode) was formed ona glass substrate, and a film of 2-TNATA was vacuum-deposited on the ITOlayer to form a hole injection layer with a thickness of 60 nm.Subsequently, NPD was vacuum-deposited with a thickness of 60 nm on thehole injection layer to form a hole transport layer. Subsequently, alight emitting layer with a thickness of 30 nm was deposited on the holetransport layer by doping the hole transport layer with the compound 1-1of the present invention as a host material andtris(2-phenylpyridine)-iridium (hereinafter abbreviated as “Ir(ppy)₃”)as a dopant material in a weight ratio of 95:5.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq₃ was formed with a thickness of 40 nm to form an electron transportlayer. Next, LiF as halogenated alkali metal was deposited with athickness of 0.2 nm on the electron transport layer to form an electroninjection layer, and then Al was deposited with a thickness of 150 nm onthe electron injection layer to form a cathode. In this way, the OLEDwas completed.

[Example 38] to [Example 192] Green Organic Light Emitting Diode (aPhosphorescent Host)

The OLEDs were manufactured in the same manner as described in Example37, except that any one of the compounds 1-2, 1-3, 1-5 to 1-7, 1-9 to1-11, 1-13 to 1-15, 1-17 to 1-19, 1-21 to 1-24, 2-1 to 2-7, 2-9 to 4-32,2-39 to 2-40, 3-1 to 3-3, 3-5 to 3-7, 3-9 to 3-11, 3-13 to 3-15, 3-17 to3-19, 3-21 to 3-24, 4-1 to 4-7, 4-9 to 4-32, 4-39, 4-40, 5-1 to 5-3, 5-5to 5-7, 5-9 to 5-11, 5-13 to 5-15, 5-17 to 5-19, 5-21 to 5-24, 6-1 to6-7, 6-9 to 6-32, 6-39, 6-40 of the present invention in the Table 5below was used as the host material of the light emitting layer, insteadof the inventive compound 1-1.

Comparative Example 7

An OLED was manufactured in the same manner as described in Example 37,except that the Comparative Compound A above was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-1.

Comparative Example 8

An OLED was manufactured in the same manner as described in Example 37,except that the Comparative Compound B above was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-1.

Comparative Example 9

An OLED was manufactured in the same manner as described in Example 37,except that the Comparative Compound C above was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-1.

Comparative Example 10

An OLED was manufactured in the same manner as described in Example 37,except that the Comparative Compound D above was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-1.

Comparative Example 11

An OLED was manufactured in the same manner as described in Example 37,except that the Comparative Compound E above was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-1.

Comparative Example 6

An OLED was manufactured in the same manner as described in Example 37,except that the Comparative Compound F above was used as the hostmaterial of the light emitting layer, instead of the inventive compound1-1.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough the Examples 37 to 192 and the Comparative Examples 7 to 12, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T90 life span was measured by life spanmeasuring equipment (Mcscience) at the reference brightness of 5000cd/m². Evaluation results are in the Table 5 below.

TABLE 5 Voltage Current Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) (x, y) Com. Ex (7) Com. Com A6.5 20.0 5000.0 25.0 73.8 (0.31, 0.60) Com. Ex (8) Com. Com B 6.5 15.15000.0 33.1 63.8 (0.31, 0.61) Com. Ex (9) Com. Com C 6.4 14.2 5000.035.3 75.7 (0.31, 0.60) Com. Ex (10) Com. Com D 6.3 13.6 5000.0 36.8 73.1(0.33, 0.61) Com. Ex (11) Com. Com E 6.2 12.9 5000.0 38.7 59.1 (0.30,0.60) Com. Ex (12) Com. Com F 6.0 12.5 5000.0 40.1 74.7 (0.31, 0.61) Ex.(37) 1-1 5.4 9.5 5000.0 52.5 140.7 (0.31, 0.60) Ex. (38) 1-2 5.3 10.05000.0 50.2 118.1 (0.33, 0.61) Ex. (39) 1-3 5.2 9.4 5000.0 53.0 141.8(0.32, 0.61) Ex. (40) 1-5 5.4 10.4 5000.0 48.0 144.6 (0.33, 0.60) Ex.(41) 1-6 5.4 11.1 5000.0 44.9 123.6 (0.32, 0.61) Ex. (42) 1-7 5.1 10.85000.0 46.4 127.5 (0.31, 0.60) Ex. (43) 1-9 5.2 11.3 5000.0 44.4 139.7(0.31, 0.61) Ex. (44) 1-10 5.3 10.4 5000.0 47.9 127.4 (0.31, 0.60) Ex.(45) 1-11 5.3 9.3 5000.0 53.6 149.6 (0.33, 0.61) Ex. (46) 1-13 5.0 11.25000.0 44.6 122.9 (0.30, 0.60) Ex. (47) 1-14 5.1 9.5 5000.0 52.5 148.1(0.31, 0.61) Ex. (48) 1-15 5.2 9.5 5000.0 52.5 123.8 (0.31, 0.60) Ex.(49) 1-17 5.0 10.1 5000.0 49.7 129.0 (0.33, 0.61) Ex. (50) 1-18 5.0 10.15000.0 49.4 110.1 (0.32, 0.61) Ex. (51) 1-19 5.2 11.6 5000.0 43.0 140.4(0.33, 0.60) Ex. (52) 1-21 5.2 11.4 5000.0 44.0 105.5 (0.32, 0.61) Ex.(53) 1-22 5.1 10.3 5000.0 48.6 123.5 (0.31, 0.60) Ex. (54) 1-23 5.1 9.95000.0 50.5 112.3 (0.31, 0.61) Ex. (55) 1-24 5.2 11.3 5000.0 44.1 115.3(0.31, 0.60) Ex. (56) 2-1 5.4 11.4 5000.0 44.0 126.4 (0.33, 0.61) Ex.(57) 2-2 5.2 10.0 5000.0 50.2 118.1 (0.30, 0.60) Ex. (58) 2-3 5.0 9.65000.0 52.1 91.9 (0.31, 0.61) Ex. (59) 2-4 5.4 9.3 5000.0 54.0 102.9(0.31, 0.60) Ex. (60) 2-5 5.5 10.9 5000.0 45.9 137.6 (0.33, 0.61) Ex.(61) 2-6 5.0 9.9 5000.0 50.4 138.3 (0.32, 0.61) Ex. (62) 2-7 5.4 10.75000.0 46.8 112.7 (0.33, 0.60) Ex. (63) 2-9 5.2 10.8 5000.0 46.3 123.6(0.31, 0.60) Ex. (64) 2-10 5.1 10.2 5000.0 49.1 148.0 (0.31, 0.61) Ex.(65) 2-11 5.3 9.1 5000.0 54.7 96.8 (0.31, 0.60) Ex. (66) 2-12 5.3 9.35000.0 53.5 100.6 (0.33, 0.61) Ex. (67) 2-13 5.2 9.3 5000.0 53.7 106.0(0.30, 0.60) Ex. (68) 2-14 5.2 9.9 5000.0 50.7 102.6 (0.31, 0.61) Ex.(69) 2-15 5.0 9.5 5000.0 52.6 108.5 (0.31, 0.60) Ex. (70) 2-16 5.2 9.75000.0 51.7 103.5 (0.33, 0.61) Ex. (71) 2-17 5.3 10.8 5000.0 46.4 127.3(0.32, 0.61) Ex. (72) 2-18 5.2 9.3 5000.0 53.9 134.2 (0.33, 0.60) Ex.(73) 2-19 5.4 11.2 5000.0 44.5 147.8 (0.32, 0.61) Ex. (74) 2-20 5.2 9.65000.0 52.1 134.4 (0.31, 0.60) Ex. (75) 2-21 5.3 11.6 5000.0 43.1 133.7(0.31, 0.61) Ex. (76) 2-22 5.0 9.3 5000.0 53.6 146.7 (0.31, 0.60) Ex.(77) 2-23 5.2 11.4 5000.0 43.9 130.3 (0.33, 0.61) Ex. (78) 2-24 5.1 11.25000.0 44.7 90.1 (0.30, 0.60) Ex. (79) 2-25 5.2 10.3 5000.0 48.6 96.7(0.31, 0.61) Ex. (80) 2-26 5.3 9.6 5000.0 52.2 138.0 (0.31, 0.60) Ex.(81) 2-27 5.0 11.3 5000.0 44.3 136.1 (0.33, 0.61) Ex. (82) 2-28 5.0 11.45000.0 44.0 125.1 (0.32, 0.61) Ex. (83) 2-29 5.4 9.7 5000.0 51.8 115.9(0.33, 0.60) Ex. (84) 2-30 5.2 9.6 5000.0 51.9 114.2 (0.32, 0.61) Ex.(85) 2-31 5.2 10.5 5000.0 47.7 95.5 (0.31, 0.60) Ex. (86) 2-32 5.3 9.65000.0 52.1 146.9 (0.31, 0.61) Ex. (87) 2-39 5.0 11.0 5000.0 45.5 145.9(0.31, 0.60) Ex. (88) 2-40 5.3 11.1 5000.0 45.0 143.1 (0.33, 0.61) Ex.(89) 3-1 5.1 10.7 5000.0 46.8 144.0 (0.31, 0.60) Ex. (90) 3-2 5.4 10.15000.0 49.5 134.0 (0.33, 0.61) Ex. (91) 3-3 5.4 10.0 5000.0 50.1 123.6(0.32, 0.61) Ex. (92) 3-5 5.3 10.3 5000.0 48.6 135.1 (0.33, 0.60) Ex.(93) 3-6 5.4 10.9 5000.0 46.0 115.5 (0.32, 0.61) Ex. (94) 3-7 5.1 10.65000.0 47.1 124.5 (0.31, 0.60) Ex. (95) 3-9 5.1 11.0 5000.0 45.4 120.1(0.31, 0.61) Ex. (96) 3-10 5.4 10.0 5000.0 50.2 97.9 (0.31, 0.60) Ex.(97) 3-11 5.2 9.6 5000.0 52.2 97.0 (0.33, 0.61) Ex. (98) 3-13 5.3 9.55000.0 52.6 99.0 (0.30, 0.60) Ex. (99) 3-14 5.4 11.5 5000.0 43.6 114.9(0.31, 0.61) Ex. (100) 3-15 5.3 11.0 5000.0 45.4 142.6 (0.31, 0.60) Ex.(101) 3-17 5.2 10.2 5000.0 48.9 104.4 (0.33, 0.61) Ex. (102) 3-18 5.19.9 5000.0 50.7 120.4 (0.32, 0.61) Ex. (103) 3-19 5.4 10.1 5000.0 49.5111.6 (0.33, 0.60) Ex. (104) 3-21 5.1 9.9 5000.0 50.6 121.6 (0.32, 0.61)Ex. (105) 3-22 5.4 9.2 5000.0 54.3 90.4 (0.31, 0.60) Ex. (106) 3-23 5.09.2 5000.0 54.4 121.2 (0.31, 0.61) Ex. (107) 3-24 5.4 10.8 5000.0 46.2129.9 (0.31, 0.60) Ex. (108) 4-1 5.0 11.5 5000.0 43.5 123.2 (0.33, 0.61)Ex. (109) 4-2 5.3 11.1 5000.0 44.9 134.4 (0.30, 0.60) Ex. (110) 4-3 5.211.1 5000.0 45.2 94.7 (0.31, 0.61) Ex. (111) 4-4 5.4 11.2 5000.0 44.5144.2 (0.31, 0.60) Ex. (112) 4-5 5.3 9.9 5000.0 50.8 115.9 (0.33, 0.61)Ex. (113) 4-6 5.2 11.5 5000.0 43.7 108.0 (0.32, 0.61) Ex. (114) 4-7 5.310.0 5000.0 50.1 119.9 (0.33, 0.60) Ex. (115) 4-9 5.2 10.1 5000.0 49.7126.1 (0.31, 0.60) Ex. (116) 4-10 5.1 10.8 5000.0 46.3 109.9 (0.31,0.61) Ex. (117) 4-11 5.3 9.2 5000.0 54.2 146.3 (0.31, 0.60) Ex. (118)4-12 5.2 10.7 5000.0 46.8 133.4 (0.33, 0.61) Ex. (119) 4-13 5.2 11.35000.0 44.1 112.3 (0.30, 0.60) Ex. (120) 4-14 5.4 10.9 5000.0 45.9 92.2(0.31, 0.61) Ex. (121) 4-15 5.2 10.6 5000.0 47.3 132.5 (0.31, 0.60) Ex.(122) 4-16 5.2 10.5 5000.0 47.5 108.4 (0.33, 0.61) Ex. (123) 4-17 5.09.7 5000.0 51.6 95.8 (0.32, 0.61) Ex. (124) 4-18 5.5 10.6 5000.0 47.1142.4 (0.33, 0.60) Ex. (125) 4-19 5.0 10.8 5000.0 46.5 128.3 (0.32,0.61) Ex. (126) 4-20 5.3 11.3 5000.0 44.1 132.5 (0.31, 0.60) Ex. (127)4-21 5.0 10.3 5000.0 48.7 106.4 (0.31, 0.61) Ex. (128) 4-22 5.1 9.35000.0 54.0 95.5 (0.31, 0.60) Ex. (129) 4-23 5.1 9.1 5000.0 54.8 114.4(0.33, 0.61) Ex. (130) 4-24 5.1 9.5 5000.0 52.4 101.6 (0.30, 0.60) Ex.(131) 4-25 5.4 10.5 5000.0 47.7 99.2 (0.31, 0.61) Ex. (132) 4-26 5.0 9.45000.0 53.4 118.4 (0.31, 0.60) Ex. (133) 4-27 5.4 9.4 5000.0 53.1 136.7(0.33, 0.61) Ex. (134) 4-28 5.4 9.4 5000.0 53.1 126.4 (0.32, 0.61) Ex.(135) 4-29 5.2 9.2 5000.0 54.1 106.6 (0.33, 0.60) Ex. (136) 4-30 5.010.1 5000.0 49.4 112.6 (0.32, 0.61) Ex. (137) 4-31 5.4 10.2 5000.0 48.9140.3 (0.31, 0.60) Ex. (138) 4-32 5.1 10.9 5000.0 45.8 92.3 (0.31, 0.61)Ex. (139) 4-39 5.3 10.9 5000.0 45.9 91.8 (0.31, 0.60) Ex. (140) 4-40 5.19.7 5000.0 51.7 112.5 (0.33, 0.61) Ex. (141) 5-1 5.2 9.8 5000.0 50.8136.7 (0.31, 0.60) Ex. (142) 5-2 5.2 10.9 5000.0 46.0 115.6 (0.33, 0.61)Ex. (143) 5-3 5.1 9.3 5000.0 53.6 110.2 (0.32, 0.61) Ex. (144) 5-5 5.010.1 5000.0 49.6 99.5 (0.33, 0.60) Ex. (145) 5-6 5.2 9.6 5000.0 51.9100.4 (0.32, 0.61) Ex. (146) 5-7 5.4 9.7 5000.0 51.6 106.8 (0.31, 0.60)Ex. (147) 5-9 5.5 9.1 5000.0 54.9 128.6 (0.31, 0.61) Ex. (148) 5-10 5.49.9 5000.0 50.6 136.1 (0.31, 0.60) Ex. (149) 5-11 5.3 9.7 5000.0 51.4149.2 (0.33, 0.61) Ex. (150) 5-13 5.3 11.6 5000.0 43.1 111.0 (0.30,0.60) Ex. (151) 5-14 5.5 10.4 5000.0 48.1 136.1 (0.31, 0.61) Ex. (152)5-15 5.4 10.6 5000.0 47.0 134.0 (0.31, 0.60) Ex. (153) 5-17 5.3 9.75000.0 51.7 125.5 (0.33, 0.61) Ex. (154) 5-18 5.3 10.1 5000.0 49.3 112.2(0.32, 0.61) Ex. (155) 5-19 5.1 10.5 5000.0 47.6 91.0 (0.33, 0.60) Ex.(156) 5-21 5.1 10.3 5000.0 48.4 94.0 (0.32, 0.61) Ex. (157) 5-22 5.0 9.45000.0 53.4 119.4 (0.31, 0.60) Ex. (158) 5-23 5.5 11.0 5000.0 45.6 104.0(0.31, 0.61) Ex. (159) 5-24 5.3 9.6 5000.0 52.0 135.5 (0.31, 0.60) Ex.(160) 6-1 5.0 10.2 5000.0 49.0 142.0 (0.33, 0.61) Ex. (161) 6-2 5.1 9.95000.0 50.5 123.9 (0.30, 0.60) Ex. (162) 6-3 5.4 10.8 5000.0 46.4 116.5(0.31, 0.61) Ex. (163) 6-4 5.3 10.8 5000.0 46.2 92.2 (0.31, 0.60) Ex.(164) 6-5 5.3 11.3 5000.0 44.3 138.4 (0.33, 0.61) Ex. (165) 6-6 5.0 9.85000.0 51.2 128.9 (0.32, 0.61) Ex. (166) 6-7 5.4 10.8 5000.0 46.3 100.2(0.33, 0.60) Ex. (167) 6-9 5.2 9.9 5000.0 50.7 134.9 (0.31, 0.60) Ex.(168) 6-10 5.1 9.4 5000.0 53.0 148.8 (0.31, 0.61) Ex. (169) 6-11 5.4 9.35000.0 53.8 106.7 (0.31, 0.60) Ex. (170) 6-12 5.1 10.1 5000.0 49.4 149.0(0.33, 0.61) Ex. (171) 6-13 5.4 10.1 5000.0 49.5 133.3 (0.30, 0.60) Ex.(172) 6-14 5.0 11.0 5000.0 45.5 147.1 (0.31, 0.61) Ex. (173) 6-15 5.010.7 5000.0 46.6 93.4 (0.31, 0.60) Ex. (174) 6-16 5.2 10.7 5000.0 46.994.8 (0.33, 0.61) Ex. (175) 6-17 5.5 10.1 5000.0 49.6 130.7 (0.32, 0.61)Ex. (176) 6-18 5.1 9.5 5000.0 52.7 145.0 (0.33, 0.60) Ex. (177) 6-19 5.29.2 5000.0 54.6 127.1 (0.32, 0.61) Ex. (178) 6-20 5.4 11.6 5000.0 43.2137.9 (0.31, 0.60) Ex. (179) 6-21 5.4 9.1 5000.0 54.8 142.9 (0.31, 0.61)Ex. (180) 6-22 5.4 10.5 5000.0 47.8 116.6 (0.31, 0.60) Ex. (181) 6-235.1 11.1 5000.0 45.0 125.9 (0.33, 0.61) Ex. (182) 6-24 5.4 11.2 5000.044.6 107.2 (0.30, 0.60) Ex. (183) 6-25 5.2 10.9 5000.0 46.0 104.6 (0.31,0.61) Ex. (184) 6-26 5.1 9.6 5000.0 52.1 133.2 (0.31, 0.60) Ex. (185)6-27 5.0 10.4 5000.0 48.0 112.5 (0.33, 0.61) Ex. (186) 6-28 5.2 11.45000.0 43.8 130.6 (0.32, 0.61) Ex. (187) 6-29 5.5 10.8 5000.0 46.3 101.5(0.33, 0.60) Ex. (188) 6-30 5.0 10.6 5000.0 47.0 115.1 (0.32, 0.61) Ex.(189) 6-31 5.4 11.6 5000.0 43.2 109.1 (0.31, 0.60) Ex. (190) 6-32 5.011.5 5000.0 43.6 125.1 (0.31, 0.61) Ex. (191) 6-39 5.1 11.1 5000.0 44.994.6 (0.31, 0.60) Ex. (192) 6-40 5.5 11.3 5000.0 44.1 117.5 (0.33, 0.61)

It can be seen from the results in Tables 4 and 5, above, that the OLEDsusing the inventive compounds as the light-emitting host material(phosphorescent host material) showed the improved efficiency, lifespanand driving voltage, compared to the OLEDs using the comparativecompounds A to F as the light-emitting host material.

That is, the OLEDs using the inventive compounds as the light-emittinghost material showed the improved results, compared to the OLEDs usingthe comparative compound A being NPB or the comparative compounds B to Fbeing the seven-membered ring. This result indicates that the electricproperties depend on the hetero atom(s) forming the ring and the fusedposition: the OLED using the comparative compound F that is aseven-membered ring comprising N and S, among the comparative compounds,showed the improved results; however, the inventive compounds comprisingN and S, like the comparative compounds, and having a differentfused-position showed improved results, compared to the comparativecompound F. This indicates that the properties of the compounds stronglydepend on the kind of the hetero atom(s) forming the ring and the fusedposition.

[Example 193] Red Organic Light Emitting Diode (Emission-AuxiliaryLayer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material

First, an ITO layer (anode) was formed on a glass substrate, and a filmof 2-TNATA was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. Subsequently, NPD wasvacuum-deposited with a thickness of 60 nm on the hole injection layerto form a hole transport layer.

Subsequently, a film of the compound 1-24 of the present invention wasvacuum-deposited on the hole transport layer to form aemission-auxiliary layer with a thickness of 20 nm.

a light emitting layer with a thickness of 30 nm was deposited on theemission-auxiliary layer by using the 4,4′-N,N′-dicarbazole-biphenyl(hereinafter abbreviated as “CBP”) as a host material and (piq)₂Ir(acac)as a dopant material in a weight ratio of 95:5.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq₃ was formed with a thickness of 40 nm to form an electron transportlayer. Next, LiF as halogenated alkali metal was deposited with athickness of 0.2 nm on the electron transport layer to form an electroninjection layer, and then Al was deposited with a thickness of 150 nm onthe electron injection layer to form a cathode. In this way, the OLEDwas completed.

[Example 194] to [Example 255] Red Organic Light Emitting Diode(Emission—Auxiliary Layer)

The OLED was manufactured in the same manner as described in TestExample 193, except that any one of the compounds 2-13 to 2-32, 3-24,4-13 to 4-32, 5-24, 6-13 to 6-32 of the present invention in the Table 6below was used as the emission-auxiliary layer material, instead of theinventive compound 1-24.

Comparative Example 13

An OLED was manufactured in the same manner as described in Test Example193, except not to form the emission-auxiliary layer.

Comparative Example 14

An OLED was manufactured in the same manner as described in Test Example193, except that Comparative Compound B above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 15

An OLED was manufactured in the same manner as described in Test Example193, except that Comparative Compound C above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 16

An OLED was manufactured in the same manner as described in Test Example193, except that Comparative Compound D above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 17

An OLED was manufactured in the same manner as described in Test Example193, except that Comparative Compound E above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 18

An OLED was manufactured in the same manner as described in Test Example193, except that Comparative Compound F above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Examples 193 to 255 and Comparative Example 13 to 18, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mcscience) at a reference brightness of 2500 cd/m².Table 6 below shows evaluation results of OLEDs manufactured TestExamples and Comparative Examples.

TABLE 6 Voltage Current Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) (x, y) Com. Ex (13) — 6.834.2 2500.0 7.3 51.6 (0.66, 0.32) Com. Ex (14) Com. Com B 6.8 27.62500.0 9.1 65.4 (0.67, 0.32) Com. Ex (15) Com. Com C 6.8 25.9 2500.0 9.653.9 (0.66, 0.32) Com. Ex (16) Com. Com D 6.9 26.8 2500.0 9.3 69.5(0.66, 0.33) Com. Ex (17) Com. Com E 6.9 26.3 2500.0 9.5 71.0 (0.65,0.32) Com. Ex (18) Com. Com F 7.0 25.1 2500.0 10.0 89.0 (0.66, 0.32) Ex.(193) 1-24 6.8 13.2 2500.0 19.0 143.9 (0.67, 0.32) Ex. (194) 2-13 6.816.4 2500.0 15.2 149.3 (0.66, 0.32) Ex. (195) 2-14 6.8 12.6 2500.0 19.891.0 (0.66, 0.32) Ex. (196) 2-15 6.9 13.4 2500.0 18.7 131.2 (0.66, 0.33)Ex. (197) 2-16 6.9 14.9 2500.0 16.7 111.6 (0.66, 0.32) Ex. (198) 2-177.0 13.2 2500.0 18.9 92.1 (0.65, 0.32) Ex. (199) 2-18 6.9 13.0 2500.019.2 103.6 (0.66, 0.32) Ex. (200) 2-19 7.0 12.8 2500.0 19.5 103.6 (0.66,0.32) Ex. (201) 2-20 6.9 13.1 2500.0 19.0 91.8 (0.67, 0.32) Ex. (202)2-21 6.8 16.2 2500.0 15.5 111.4 (0.66, 0.32) Ex. (203) 2-22 6.9 15.22500.0 16.5 115.7 (0.67, 0.32) Ex. (204) 2-23 6.8 14.7 2500.0 17.0 142.0(0.66, 0.32) Ex. (205) 2-24 6.9 12.6 2500.0 19.9 135.0 (0.66, 0.32) Ex.(206) 2-25 6.9 15.8 2500.0 15.8 94.6 (0.66, 0.33) Ex. (207) 2-26 6.915.2 2500.0 16.5 98.8 (0.66, 0.32) Ex. (208) 2-27 7.0 12.8 2500.0 19.5131.6 (0.65, 0.32) Ex. (209) 2-28 6.9 13.7 2500.0 18.2 141.9 (0.66,0.32) Ex. (210) 2-2) 6.9 12.9 2500.0 19.4 97.5 (0.66, 0.32) Ex. (211)2-30 6.9 15.7 2500.0 16.0 124.4 (0.67, 0.32) Ex. (212) 2-31 6.8 14.42500.0 17.4 97.8 (0.66, 0.32) Ex. (213) 2-32 6.9 14.0 2500.0 17.9 137.0(0.67, 0.32) Ex. (214) 3-24 6.9 15.3 2500.0 16.3 98.2 (0.66, 0.32) Ex.(215) 4-13 6.9 14.3 2500.0 17.4 103.3 (0.66, 0.32) Ex. (216) 4-14 6.914.0 2500.0 17.8 116.5 (0.66, 0.33) Ex. (217) 4-15 6.9 13.7 2500.0 18.392.8 (0.66, 0.32) Ex. (218) 4-16 6.9 12.7 2500.0 19.7 142.7 (0.65, 0.32)Ex. (219) 4-17 6.8 16.5 2500.0 15.1 147.2 (0.66, 0.32) Ex. (220) 4-186.9 16.2 2500.0 15.4 141.6 (0.66, 0.32) Ex. (221) 4-19 6.9 16.0 2500.015.6 126.5 (0.67, 0.32) Ex. (222) 4-20 6.9 13.4 2500.0 18.7 145.7 (0.66,0.32) Ex. (223) 4-21 6.9 16.3 2500.0 15.4 134.4 (0.67, 0.32) Ex. (224)4-22 6.9 14.7 2500.0 17.0 142.4 (0.66, 0.32) Ex. (225) 4-23 7.0 13.62500.0 18.3 117.3 (0.67, 0.32) Ex. (226) 4-24 6.9 14.7 2500.0 17.0 92.2(0.66, 0.32) Ex. (227) 4-25 6.9 16.0 2500.0 15.6 98.5 (0.66, 0.33) Ex.(228) 4-26 7.0 14.8 2500.0 16.9 136.4 (0.65, 0.32) Ex. (229) 4-27 6.815.8 2500.0 15.8 135.9 (0.66, 0.32) Ex. (230) 4-28 6.9 13.2 2500.0 18.999.2 (0.67, 0.32) Ex. (231) 4-29 6.9 16.5 2500.0 15.1 121.3 (0.66, 0.32)Ex. (232) 4-30 6.8 15.0 2500.0 16.7 132.9 (0.66, 0.32) Ex. (233) 4-316.9 13.1 2500.0 19.0 91.5 (0.66, 0.33) Ex. (234) 4-32 6.9 14.6 2500.017.2 108.5 (0.66, 0.32) Ex. (235) 5-24 6.9 12.5 2500.0 20.0 135.0 (0.65,0.32) Ex. (236) 6-13 6.9 16.4 2500.0 15.2 133.6 (0.66, 0.32) Ex. (237)6-14 6.9 13.9 2500.0 18.0 135.7 (0.66, 0.32) Ex. (238) 6-15 7.0 13.42500.0 18.7 101.7 (0.67, 0.32) Ex. (239) 6-16 6.8 13.6 2500.0 18.3 91.5(0.66, 0.32) Ex. (240) 6-17 6.9 14.1 2500.0 17.7 92.0 (0.67, 0.32) Ex.(241) 6-18 6.9 12.9 2500.0 19.4 98.4 (0.66, 0.32) Ex. (242) 6-19 7.013.4 2500.0 18.6 113.3 (0.66, 0.32) Ex. (243) 6-20 6.9 13.1 2500.0 19.193.0 (0.66, 0.33) Ex. (244) 6-21 7.0 13.2 2500.0 18.9 109.9 (0.66, 0.32)Ex. (245) 6-22 6.8 15.4 2500.0 16.2 100.8 (0.65, 0.32) Ex. (246) 6-236.8 15.4 2500.0 16.2 112.3 (0.66, 0.32) Ex. (247) 6-24 6.9 13.3 2500.018.7 96.1 (0.66, 0.32) Ex. (248) 6-25 7.0 13.3 2500.0 18.8 112.5 (0.67,0.32) Ex. (249) 6-26 7.0 13.6 2500.0 18.4 123.4 (0.66, 0.32) Ex. (250)6-27 6.9 14.6 2500.0 17.2 121.0 (0.67, 0.32) Ex. (251) 6-28 6.9 16.42500.0 15.3 97.2 (0.66, 0.32) Ex. (252) 6-29 7.0 13.8 2500.0 18.1 121.6(0.66, 0.32) Ex. (253) 6-30 7.0 16.5 2500.0 15.1 109.5 (0.66, 0.33) Ex.(254) 6-31 6.9 16.1 2500.0 15.6 132.7 (0.66, 0.32) Ex. (255) 6-32 6.914.9 2500.0 16.8 113.1 (0.65, 0.32)

[Example 256] Green Organic Light Emitting Diode (an Emission-AuxiliaryLayer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material

First, an ITO layer (anode) was formed on a glass substrate, and a filmof 2-TNATA was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. Subsequently, NPD wasvacuum-deposited with a thickness of 60 nm on the hole injection layerto form a hole transport layer.

Subsequently, a film of the compound 1-24 of the present invention wasvacuum-deposited on the hole transport layer to form aemission-auxiliary layer with a thickness of 20 nm. A light emittinglayer with a thickness of 30 nm was deposited on the emission-auxiliarylayer by using the CBP as a host material and Ir(ppy)₃ as a dopantmaterial in a weight ratio of 95:5.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq₃ was formed with a thickness of 40 nm to form an electron transportlayer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

[Example 257] to [Example 318] Green Organic Light Emitting Diode (anEmission-Auxiliary Layer)

The OLED was manufactured in the same manner as described in TestExample 256, except that any one of the compounds 2-13 to 2-32, 3-24,4-13 to 4-32, 5-24, 6-13 to 6-32 of the present invention in the Table 7below was used as the emission-auxiliary layer material, instead of theinventive compound 1-24.

Comparative Example 19

An OLED was manufactured in the same manner as described in Test Example256, except not to form the emission-auxiliary layer.

Comparative Example 20

An OLED was manufactured in the same manner as described in Test Example256, except that Comparative Compound B above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 21

An OLED was manufactured in the same manner as described in Test Example256, except that Comparative Compound C above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 22

An OLED was manufactured in the same manner as described in Test Example256, except that Comparative Compound D above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 23

An OLED was manufactured in the same manner as described in Test Example256, except that Comparative Compound E above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

Comparative Example 24

An OLED was manufactured in the same manner as described in Test Example256, except that Comparative Compound F above was used as theemission-auxiliary layer material, instead of the inventive compound1-24.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Examples 256 to 318 and Comparative Example 19 to 24, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mcscience) at a reference brightness of 5000 cd/m².Table 7 below shows evaluation results of OLEDs manufactured TestExamples and Comparative Examples.

TABLE 7 Voltage Current Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) (x, y) Com. Ex (19) — 6.520.0 5000.0 25.0 73.8 (0.31, 0.60) Com. Ex (20) Com. Com B 6.8 13.05000.0 38.4 80.4 (0.31, 0.61) Com. Ex (21) Com. Com C 7.0 13.9 5000.036.0 85.3 (0.31, 0.60) Com. Ex (22) Com. Com D 6.7 13.6 5000.0 36.9 85.5(0.33, 0.61) Com. Ex (23) Com. Com E 7.0 13.0 5000.0 38.5 84.3 (0.30,0.60) Com. Ex (24) Com. Com F 6.6 13.4 5000.0 37.3 83.6 (0.31, 0.61) Ex.(256) 1-24 6.8 9.1 5000.0 54.7 111.5 (0.31, 0.60) Ex. (257) 2-13 6.811.1 5000.0 45.1 147.6 (0.33, 0.61) Ex. (258) 2-14 6.8 10.7 5000.0 46.7129.7 (0.32, 0.61) Ex. (259) 2-15 6.9 9.5 5000.0 52.9 137.2 (0.33, 0.60)Ex. (260) 2-16 6.6 10.9 5000.0 46.0 114.4 (0.32, 0.61) Ex. (261) 2-176.7 10.5 5000.0 47.8 125.5 (0.31, 0.60) Ex. (262) 2-18 6.6 10.1 5000.049.5 111.8 (0.31, 0.61) Ex. (263) 2-19 6.6 9.7 5000.0 51.6 137.3 (0.31,0.60) Ex. (264) 2-20 6.8 9.5 5000.0 52.4 108.6 (0.33, 0.61) Ex. (265)2-21 6.5 11.0 5000.0 45.7 144.1 (0.30, 0.60) Ex. (266) 2-22 7.0 10.45000.0 48.3 145.5 (0.31, 0.61) Ex. (267) 2-23 6.6 10.3 5000.0 48.5 147.3(0.31, 0.60) Ex. (268) 2-24 6.6 9.1 5000.0 55.0 142.1 (0.33, 0.61) Ex.(269) 2-25 6.8 10.5 5000.0 47.7 92.0 (0.32, 0.61) Ex. (270) 2-26 6.610.1 5000.0 49.5 96.7 (0.33, 0.60) Ex. (271) 2-27 6.9 9.2 5000.0 54.6144.3 (0.32, 0.61) Ex. (272) 2-28 6.9 10.0 5000.0 49.9 103.5 (0.31,0.60) Ex. (273) 2-29 6.7 9.4 5000.0 53.2 93.1 (0.31, 0.61) Ex. (274)2-30 6.6 11.0 5000.0 45.6 135.7 (0.31, 0.60) Ex. (275) 2-31 6.8 10.05000.0 50.2 108.4 (0.33, 0.61) Ex. (276) 2-32 7.0 10.8 5000.0 46.4 149.4(0.30, 0.60) Ex. (277) 3-24 6.8 9.9 5000.0 50.5 120.4 (0.31, 0.61) Ex.(278) 4-13 7.0 9.2 5000.0 54.6 117.8 (0.31, 0.60) Ex. (279) 4-14 6.5 9.15000.0 54.7 105.8 (0.33, 0.61) Ex. (280) 4-15 6.9 10.8 5000.0 46.2 125.1(0.32, 0.61) Ex. (281) 4-16 6.6 11.0 5000.0 45.5 116.9 (0.33, 0.60) Ex.(282) 4-17 6.9 10.6 5000.0 47.3 90.8 (0.31, 0.60) Ex. (283) 4-18 6.9 9.15000.0 54.9 140.7 (0.31, 0.61) Ex. (284) 4-19 6.8 10.6 5000.0 47.1 141.8(0.31, 0.60) Ex. (285) 4-20 6.9 11.1 5000.0 45.2 134.9 (0.33, 0.61) Ex.(286) 4-21 6.9 9.7 5000.0 51.5 110.7 (0.30, 0.60) Ex. (287) 4-22 7.0 9.85000.0 51.1 93.7 (0.31, 0.61) Ex. (288) 4-23 6.8 9.5 5000.0 52.9 105.9(0.31, 0.60) Ex. (289) 4-24 7.0 9.7 5000.0 51.5 110.7 (0.33, 0.61) Ex.(290) 4-25 6.9 9.3 5000.0 53.8 122.4 (0.32, 0.61) Ex. (291) 4-26 6.8 9.85000.0 51.0 94.4 (0.33, 0.60) Ex. (292) 4-27 6.9 10.5 5000.0 47.6 102.8(0.32, 0.61) Ex. (293) 4-28 6.6 9.4 5000.0 53.4 98.7 (0.31, 0.60) Ex.(294) 4-29 6.6 10.9 5000.0 45.7 129.0 (0.31, 0.61) Ex. (295) 4-30 6.610.2 5000.0 48.8 125.1 (0.31, 0.60) Ex. (296) 4-31 6.7 10.5 5000.0 47.4133.2 (0.33, 0.61) Ex. (297) 4-32 6.6 11.1 5000.0 45.0 124.7 (0.30,0.60) Ex. (298) 5-24 6.5 9.1 5000.0 54.8 92.3 (0.31, 0.61) Ex. (299)6-13 7.0 9.8 5000.0 50.9 91.4 (0.31, 0.60) Ex. (300) 6-14 6.6 9.5 5000.052.8 119.5 (0.33, 0.61) Ex. (301) 6-15 6.5 11.0 5000.0 45.4 129.4 (0.32,0.61) Ex. (302) 6-16 7.0 9.6 5000.0 52.3 132.2 (0.33, 0.60) Ex. (303)6-17 6.6 9.4 5000.0 53.4 118.4 (0.32, 0.61) Ex. (304) 6-18 7.0 9.55000.0 52.5 92.7 (0.31, 0.60) Ex. (305) 6-19) 6.8 10.4 5000.0 48.3 129.7(0.31, 0.61) Ex. (306) 6-20 7.0 10.5 5000.0 47.5 131.8 (0.31, 0.60) Ex.(307) 6-21 6.8 10.2 5000.0 49.1 148.2 (0.33, 0.61) Ex. (308) 6-22 6.910.6 5000.0 47.1 105.1 (0.31, 0.60) Ex. (309) 6-23 7.0 10.1 5000.0 49.7114.0 (0.33, 0.61) Ex. (310) 6-24 6.5 10.2 5000.0 48.9 134.5 (0.32,0.61) Ex. (311) 6-25 6.5 11.1 5000.0 45.2 142.9 (0.33, 0.60) Ex. (312)6-26 6.9 9.5 5000.0 52.8 108.2 (0.32, 0.61) Ex. (313) 6-27 6.9 11.05000.0 45.3 98.4 (0.31, 0.60) Ex. (314) 6-28 6.6 9.5 5000.0 52.7 109.0(0.31, 0.61) Ex. (315) 6-29 6.8 11.0 5000.0 45.4 143.0 (0.31, 0.60) Ex.(316) 6-30 6.7 10.1 5000.0 49.3 149.2 (0.33, 0.61) Ex. (317) 6-31 6.810.1 5000.0 49.4 125.0 (0.30, 0.60) Ex. (318) 6-32 6.8 10.0 5000.0 50.2136.8 (0.31, 0.61)

It can be seen from the resulting data in Tables 6 and 7, above, thatthe efficiency and lifespan of the OLEDs having the inventive compoundsas the material of the emission-auxiliary layer were remarkablyimproved, compared to the OLEDs not having the emission-auxiliary layer,or the comparative compounds B to F.

The driving voltage of the OLED comprising the emission-auxiliary layerwas equal to or slightly higher than the OLED not having theemission-auxiliary layer, but the OLED comprising the emission-auxiliarylayer showed improvement in efficiency and lifespan. That is, theinventive compounds showed improved efficiency and lifespan, compared tothe comparative compounds B to F. It is believed this is because theinventive compound has the high T1 energy level and the deep HOMO energylevel when it is used alone as the material of the emission-auxiliarylayer, and as a result, the holes and the electrons achieve the chargebalance, and thus the light emission is made efficiently in the lightemitting layer, not in the interface of the hole transport layer, andthus the efficiency and lifespan are improved. Further, as explained inTables 4 and 5, the electric properties of OLEDs are different dependingon the kind of the heteroatom and the fused position even in a similarseven-membered ring compound, which suggests that the properties of thecompounds remarkably depend on the kind of the atom(s) in theheterocyclic ring and the fused position.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

The invention claimed is:
 1. A compound of Formula 1:

wherein: Z is S, one of X, Y, V and W is N(R⁶), and the other three ofX, Y, V and W are each independently S or O, m, n, o and p are eachindependently an integer of 0 or 1, with the proviso that m+n is 1 ormore and o+p is 1 or more, R¹ to R⁴ are each independently selected fromthe group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si and P; afused ring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group;-L′-N(Ar¹)(Ar²); and a combination thereof, a and d are each an integerof 0 to 4, b and c are each an integer of 0 to 2, and where a, b, c or dis 2 or more, two adjacent groups of R¹s, R²s, R³s or R⁴s are optionallylinked together to form a ring, R⁶ is selected from the group consistingof a fluorenyl group; a C₈-C₆₀ heterocyclic group containing aquinazolinyl group; and -L′-N(Ar¹)(Ar²), with the proviso that where L′is a single bond or a C₆ aryl group in the -L′-N(Ar¹)(Ar²), at least oneof Ar¹ a Ar² is a fluorenyl group or a C₂-C₆₀ heterocyclic group; L′ isselected from the group consisting of a single bond; a C₆-C₆₀ arylenegroup; a fluorenylene group; a fused ring group formed by a C₃-C₆₀aliphatic ring with a C₆-C₆₀ aromatic ring; a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P; and a combination thereof, wherein, L′ may beoptionally substituted by one or more substituents selected from thegroup consisting of deuterium; halogen; a silane group; a siloxanegroup; a boron group; a germanium group; a cyano group; a nitro group; aC₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; aC₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; a C₃-C₂₀ cycloalkylgroup; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀ arylalkenyl group, Ar¹ andAr² are each independently selected from the group consisting of aC₆-C₆₀ aryl group; a fluorenyl group; a fused ring group formed by aC₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring; a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P; and a combination thereof, and whereR¹ to R⁴, Ar¹ and Ar² are the aryl, fluorenyl, heterocyclic ring orfused ring, and where R⁶ is the fluorenyl or heterocyclic ring each ofthe R¹ to R⁴ and R⁶, Ar¹, and Ar² is optionally substituted with one ormore substituents selected from the group consisting of deuterium;halogen; a silane group; a siloxane group; a boron group; a germaniumgroup; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.
 2. A compound of Formula 1:

wherein: Z is N(R⁵), X, Y, V and W are each independently N(R⁶), S or O,with the proviso that: at least one of X, Y, V and W is not N(R⁶), andwhere both n and o are 0 (zero), at least one of Y and V is not N(R⁶),m, n, o and p are each independently an integer of 0 or 1, with theproviso that m+n is 1 or more and o+p is 1 or more, R¹ to R⁴ are eachindependently selected from the group consisting of deuterium; halogen;a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P; a fused ring group formed by a C₃-C₆₀ aliphatic ringwith a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxygroup; -L-N(Ar¹)(Ar²); and a combination thereof, a and d are each aninteger of 0 to 4, b and c are each an integer of 0 to 2, and where a,b, c or d is 2 or more, two adjacent groups of R¹s, R²s, R³s or R⁴s areoptionally linked together to form a ring except for a heterocyclicgroup containing O, R⁵ is a C₂-C₆₀ heterocyclic group containing aquinazolinyl group, R⁶ is selected from the group consisting of a C₆-C₆₀aryl group; a fluorenylene group; or a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P; a fused ring group formed by a C₃-C₆₀ aliphatic ringwith a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxygroup; -L′-N(Ar¹)(Ar²); and a combination thereof, L′ is selected fromthe group consisting of a single bond; a C₆-C₆₀ arylene group; afluorenylene group; a fused ring group formed by a C₃-C₆₀ aliphatic ringwith a C₆-C₆₀ aromatic ring; a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P; and a combination thereof, Ar¹ and Ar² are each independentlyselected from the group consisting of a C₆-C₆₀ aryl group; a fluorenylgroup; a fused ring group formed by a C₃-C₆₀ aliphatic ring with aC₆-C₆₀ aromatic ring; a C₂-C₆₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si, and P;and a combination thereof, with the proviso that where X, Y, V and W areeach 0 or S, the R⁵ is a C₁₀-C₆₀ fused aryl group, a fluorenyl group, aC₈ heterocyclic group, or -L′-N(Ar¹)(Ar²), wherein where L′ is a singlebond or a C₆ arylene group, at least one of Ar¹ and Ar² is selected fromthe group consisting of a C₁₀-C₆₀ aryl group, a fluorenyl group; a fusedring group formed by a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromaticring; a C₂-C₆₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P; and acombination thereof, and where R¹ to R⁴ and R⁶, L′, Ar¹ and Ar² are thearyl, fluorenyl, heterocyclic ring or fused ring, and where R⁵ is thefluorenyl or heterocyclic group, each of the R¹ to R⁶, Ar¹, and Ar², isoptionally substituted with one or more substituents selected from thegroup consisting of deuterium; halogen; a silane group; a siloxanegroup; a boron group; a germanium group; a cyano group; a nitro group; aC₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; aC₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; aC₂-C₂₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; a C₃-C₂₀ cycloalkylgroup; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀ arylalkenyl group.
 3. Thecompound of claim 1 represented by one of Formulas 2 to 4:

wherein V, W, X, Y, Z, R¹ to R⁴, a, b, c and d are defined the same asin claim
 1. 4. The compound of claim 2 represented by one of Formulas 2to 4:

wherein V, W, X, Y, Z, R¹ to R⁴, a, b, c and d are defined the same asin claim
 2. 5. A compound selected from the group consisting of:


6. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode and comprising one or more of thecompounds of claim
 1. 7. An organic electric element comprising a firstelectrode, a second electrode, and an organic material layer disposedbetween the first electrode and the second electrode and comprising oneor more of the compounds of claim
 2. 8. An organic electric elementcomprising a first electrode, a second electrode, and an organicmaterial layer disposed between the first electrode and the secondelectrode and comprising one or more of the compounds of claim
 5. 9. Theorganic electric element of claim 6, wherein the organic material layercomprises at least one of a hole injection layer, a hole transportlayer, an emission-auxiliary layer and a light emitting layer.
 10. Theorganic electric element of claim 7, wherein the organic material layercomprises at least one of a hole injection layer, a hole transportlayer, an emission-auxiliary layer and a light emitting layer.
 11. Theorganic electric element of claim 6, wherein the organic electricelement further comprises a luminescence efficiency-improving layerformed on the surface of the first and/or the second electrodes notcontacting the organic material layer.
 12. The organic electric elementof claim 7, wherein the organic electric element further comprises aluminescence efficiency-improving layer formed on the surface of thefirst and/or the second electrodes not contacting the organic materiallayer.
 13. An electronic device comprising a display device, whichcomprises the organic electric element of claim 6, and a control unitfor driving the display device.
 14. An electronic device comprising adisplay device, which comprises the organic electric element of claim 7,and a control unit for driving the display device.
 15. An electronicdevice comprising a display device, which comprises the organic electricelement of claim 8, and a control unit for driving the display device.16. The electronic device of claim 14, wherein the organic electricelement comprises at least one of an organic light emitting diode, anorganic solar cell, an organic photo conductor, an organic transistor,and an element for monochromatic or white illumination.
 17. Theelectronic device of claim 15, wherein the organic electric elementcomprises at least one of an organic light emitting diode, an organicsolar cell, an organic photo conductor, an organic transistor, and anelement for monochromatic or white illumination.